Organic Chemistry Test Bank Smith 5 ED.

Test Bank of Organic Chemistry 4th
Edition By Janice Smith
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Chapter 1: Structure and Bonding
1. What is the ground-state electronic configuration of a carbon atom?

A) 1s2, 2s2, 2p5 B) 1s2, 2s2, 2p2 C) 1s2, 2s2, 2p6 D) 1s2, 2s2, 2p4
2. What is the ground-state electronic configuration of a fluorine atom?

A) 1s2, 2s2, 2p2 B) 1s2, 2s2, 2p3 C) 1s2, 2s2, 2p4 D) 1s2, 2s2, 2p5
3. What is the ground-state electronic configuration of a magnesium cation (Mg2+)?

A) 1s2, 2s2, 2p6 C) 1s2, 2s2, 2p6, 3s2
B) 1s2, 2s2, 2p6, 3s1 D) 1s2, 2s2, 2p6, 3s2, 3p2
4. What is the ground-state electronic configuration of a chlorine anion (Cl—)?

A) 1s2, 2s2, 2p6 C) 1s2, 2s2, 2p6, 3s2, 3p5
B) 1s2, 2s2, 2p6, 3s2, 3p6 D) 1s2, 2s2, 2p6, 3s2, 3p4
5. Which of the following statements about valence electrons is true?

A) They are the most tightly held electrons.
B) They do not participate in chemical reactions.
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C) They are the outermost electrons.

D) They reveal the period number of a second-row element.
6. Which of the following statements about bonding is true?

A) Covalent bonds result from the transfer of electrons from one element to another.
B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.
C) Ionic bonds result from the sharing of electrons between two non-metals.
D) Covalent bonds result from the sharing of electrons between two metals.
7. Which of the following would you expect to have ionic bonds?

A) CO B) FBr C) NF3 D) NaCl
8. Which of the following molecules has nonpolar covalent bonds?

A) HCl B) N2 C) CHCl3 D) NO
9. Which of the following molecules contain both covalent and ionic bonds?
A) I, II B) I, IV C) II, III D) II, IV
10. Arrange the following bonds in decreasing order of ionic character, putting the most
ionic first.
A) I > II > III > IV C) IV > III > II > I

B) IV > II > I > III D) IV > II > III > I
11. Which of the following statements correctly describes the typical number of bonds for
carbon, nitrogen, and oxygen in most neutral organic molecules?
A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds and oxygen forms
3 covalent bonds.
B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms
2 covalent bonds.
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C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms
2 covalent bonds.
D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms
4 covalent bonds.
12. Which is not an acceptable Lewis structure for the anion CH2NCO—?
A) I B) II C) III D) IV
13. Which of the following Lewis structures is correct?
14. Which of the following Lewis structures is correct?
A) I, II B) I, III C) II, III D) III, IV
15. Which is the correct Lewis structure for acetic acid (CH3CO2H)?
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16. In which of the following ions does carbon have a formal charge?
A) I B) II C) III D) None of the above
17. In which of the following ions does carbon have a formal charge?
18. What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple
bond?
A) 0 B) -2 C) -1 D) +1
19. Which of the following statements about constitutional isomers is true?

A) Constitutional isomers are different molecules having different molecular formula.
B) Constitutional isomers are different molecules having same molecular formula.
C) Constitutional isomers are same molecules having different molecular formula.
D) Constitutional isomers are same molecules having the same molecular formula.
20. How many constitutional isomers are there for a molecule having the molecular formula
C2H6O?
A) 1 B) 2 C) 3 D) 4
21. How many constitutional isomers are there for a molecule having the molecular C3H8O?
A) 1 B) 2 C) 3 D) 4
C3H6?
A) 1 B) 2 C) 3 D) 4
C2H4Cl2?
A) 1 B) 2 C) 3 D) 4
24. How many different isomers are there for a compound having the molecular formula
C3H6O?
A) 4 B) 5 C) 6 D) 7
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25. Which of the following molecules are constitutional isomers?
A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III
26. Which of the following compounds has an atom with an unfilled valence shell of
electrons?
A) H2O B) BCl3 C) CH4 D) CO2
27. Which of the following statements about resonance structures is true?

A) Resonance structures have the same placement of electrons but different
arrangement of atoms.
B) Resonance structures have the same placement of atoms but different arrangement
of electrons.
C) Resonance structures have the same placement of atoms and the same arrangement
of electrons.
D) Resonance structures have different placement of atoms and different arrangement
of electrons.
28. Which of the following statements about resonance structures is not true?
A) There is no movement of electrons from one form to another.
B) Resonance structures are not isomers.
C) Resonance structures differ only in the arrangement of electrons.
D) Resonance structures are in equilibrium with each other.
29. Which of the following pair does not represent resonance structures?
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30. What 2 things will change between two resonance structures?

A) The position of multiple bonds and non-bonded electrons.
B) The position of multiple bonds and single bonds.
C) The placement of atoms and single bonds.
D) The placement of atoms and non-bonded electrons.
31. Which of the following is a resonance structure of the compound below?
32. Which of the following resonance structures is the least important contributor to the
resonance hybrid of the formate anion, HCOO—?
33. Rank the following in order of decreasing importance as contributing structures to the
resonance hybrid of formaldehyde, H2CO.
A) I > II > III B) I > III > II C) II > I > III D) III > II > I
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34. Follow the curved arrows to draw the second resonance structure for the ion below.
35. Which is more important in each pair of contributing resonance structures?
A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V
36. What is the approximate value of the H-C-H bond angle in methane, CH4?
A) 90° B) 109.5° C) 120° D) 180°
37. What is the approximate C-C-C bond angle in propene, CH3CH=CH2?

A) 90° B) 109.5° C) 120° D) 180°
38. What is the approximate H-C-O bond angle in formaldehyde, H2CO?

A) 90° B) 109.5° C) 120° D) 180°
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39. Determine the electron geometry around the indicated atom in each species.
A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral

B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear
C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar
D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral
40. What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN?
A) 90° B) 109.5° C) 120° D) 180°
41. Which of the following is the appropriate conversion of the condensed structure,
CH3COCH3, to a Lewis structure?
42. Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a

skeletal structure?
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43. Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?
44. What is the condensed formula of the compound below?
45. Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a

skeletal structure?
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46. Convert the following skeletal structure to a condensed structure.
47. Avobenzone is an active ingredient in some common sunscreens. Which of the

following is the correct molecular formula for avobenzone?
A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3
48. In which structure is the hybridization incorrect?
49. What is the hybridization for each of the indicated atoms in the following compound?
A) I = sp2; II = sp2; III = sp2. C) I = sp; II = sp2; III = sp3.
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B) I = sp2; II = sp3; III = sp3. D) I = sp2; II = sp2; III = sp3.
50. What is the hybridization of the carbon atom in the methyl cation, (CH3+)?
A) sp3 B) sp2 C) sp D) p
51. What is the hybridization of the nitrogen atom in the ammonium cation, NH4+?
52. Which atomic orbitals overlap to form the C-H  bonding molecular orbitals of ethane,
CH3CH3?
A) Csp2 + H1s B) Csp3 + H1s C) C2p + H1s D) Csp + H1s
53. Which atomic orbitals overlap to form the C-H  bonding molecular orbitals of
ethylene, H2C=CH2?
A) C2p + H1s B) Csp + H1s C) Csp3 + H1s D) Csp2 + H1s
54. Which atomic orbitals overlap to form the carbon-carbon  and  bonding molecular
orbitals of ethylene, H2C=CH2?
A) Csp3 + Csp3, and C2p + C2p C) Csp2 + Csp2, and C2p + C2p
B) Csp3 + Csp3, and Csp2 + Csp2 D) Csp2 + Csp2, and Csp2 + Csp2
55. Which atomic orbitals overlap to form the C-H  bonding molecular orbitals of
acetylene, C2H2?
A) Csp + H1s B) C2p +H1s C) Csp3 + H1s D) Csp2 + H1s
56. Which atomic orbitals overlap to form the carbon-carbon  bonding molecular orbital of
acetylene, C2H2?
A) Csp2 + Csp2 B) Csp + Csp C) Csp3 + Csp3 D) C2p + C2p
57. When forming molecular orbitals from atomic orbitals, what is the order of increasing
C-H bond strength for the following.
A) II III > II B) I > II > III C) III > II > I D) II > III > I
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59. Which of the following statements about electronegativity and the periodic table is true?
A) Electronegativity decreases across a row of the periodic table.
B) Electronegativity increases down a column of the periodic table.
C) Electronegativity increases across a row of the periodic table.
D) Electronegativity does not change down a column of the periodic table.
60. Rank the following atoms in order of increasing electronegativity, putting the least
electronegative first.
A) I < II < III < IV C) III < II < IV IV > II > III C) III > IV > II > I

B) II > III > IV > I D) III > II > IV > I
62. Which molecule has the greatest difference in electronegativity (E) between the two
different elements?
A) CO2 B) H2S C) NH3 D) H2O
63. Which compound contains the most polar bond?
64. Which of the following compounds are non-polar?
A) I, IV B) I, II C) II, III D) II, IV
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65. Which of the following molecules has non-polar covalent bonds?

A) CO2 B) N2 C) CCl4 D) HF
66. Which of the following molecules has polar covalent bonds?

A) MgO B) NH3 C) Cl2 D) NaBr
67. Which of the following covalent bonds has the largest dipole moment?
A) C-H B) C-C C) C-O D) H-F
68. Which of the following molecules has the smallest dipole moment?
A) CO2 B) HCl C) H2O D) NH3
69. Which of the following molecules does not have a net dipole moment of zero?
A) CCl4 B) BF3 C) CO2 D) NH3
70. Which of the following molecules has a net dipole moment of zero?
Chapter 2: Acids and Bases
1. Which of the following statements is a correct definition for a Brønsted-Lowry acid?

A) Proton acceptor C) Electron pair acceptor
B) Electron pair donor D) Proton donor
2. Which of the following statements about a Brønsted-Lowry base is true?

A) The net charge may be zero, positive, or negative.
B) All Brønsted-Lowry bases contain a lone pair of electrons or a  bond.
C) All Brønsted-Lowry bases contain a proton.
D) The net charge may be zero or positive.
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3. Which of the following compounds is both a Brønsted-Lowry acid and base?
A) I, II B) I, III C) II, IV D) I, IV
4. Which of the following species cannot act as both a Brønsted-Lowry acid and base?
A) HCO3- B) HSO4- C) HO- D) H2PO4-
5. Which of the following species is not a Brønsted-Lowry base?

A) BF3 B) NH3 C) H2O D) PO43-
6. Which of the following statements about Brønsted-Lowry acids and bases is true?
A) Loss of a proton from a base forms its conjugate acid.
B) Loss of a proton from an acid forms its conjugate base.
C) Gain of a proton by an acid forms its conjugate base.
D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a
base to an acid.
7. Which of the following species is the conjugate base of methanol, CH3OH?

A) CH3OH2+ B) CH3O- C) CH3- D) CH4
8. Which of the following species is the conjugate base of the hydronium ion, H3O+?
A) H3O B) H2O- C) H2O D) HO-
9. Which of the following species is the conjugate acid of ammonia, NH3?

A) H4N B) H3N+ C) H2N- D) H4N+
10. Which is the conjugate acid in the following reaction?
11. Which is the conjugate base in the following reaction?
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12. Which is the conjugate acid in the following reaction?
13. Which is the conjugate base in the following reaction?
14. Which of the following statements about acid strength is true?

A) The stronger the acid, the further the equilibrium lies to the left.
B) The stronger the acid, the smaller the Ka.
C) The stronger the acid, the larger the pKa.
D) The stronger the acid, the smaller the pKa.
15. Which of the following compounds is the strongest acid?
16. Which of the following compounds is the strongest acid?

A) CH3OH B) BrCH2OH C) CH3NH2 D) CH3Cl
17. Which of the following compounds is the weakest acid?

A) HF B) HCl C) HBr D) HI
18. Which of the following compounds is the weakest acid?

A) H2S B) PH3 C) HCl D) SiH4
19. Which of the following species is the strongest base?

A) HO- B) H2N- C) CH3COO- D) Cl-
20. Which of the following ranks the compounds in order of increasing basicity, putting the
least basic first?
A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
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B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2
21. Consider the following molecule with protons labeled, I-III. Rank these protons in
order of decreasing acidity, putting the most acidic first.
A) I > II > III B) I > III > II C) III > II > I D) III > I > II
22. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
A) III < I < IV < II C) II < I < IV < III

B) III < IV < I < II D) III < I < II < IV
first.
A) I < IV < III < II C) II < III < IV II > III > I C) I > II > IV > III
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B) III > II > IV > I D) III > IV > II > I
first.
A) IV > II > III > I C) III > IV > II > I

B) IV > III > II > I D) III > IV > I > II
26. Rank the following conjugate bases in order of increasing basicity, putting the least
basic first.
A) II I > III B) I > II > III C) III > I > II D) III > II > I
28. Which of the following is the strongest base?

A) CH3COCH3 B) CH3COOH C) NH3 D) H2O
29. What is the direction of equilibrium when acetylene (C2H2) reacts with H2N- in an acid-
base reaction?
A) Left B) Right C) Neither D) Cannot be determined
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30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide
(CH3CH2O-) in an acid-base reaction?
A) Left B) Right C) Neither D) Cannot be determined
31. Which of the following statements explain why H2O is a stronger acid than CH4?
A) H2O can form hydrogen bonds while CH4 cannot.
B) H2O forms a less stable conjugate base, HO-.
C) CH4 forms a more stable conjugate base, CH3-.
D) H2O forms a more stable conjugate base, HO-.
32. Which of the following statements explain why HBr is a stronger acid than HF?
A) Br- is more stable than F- because Br- is larger than F-.
B) Br- is less stable than F- because Br- is larger than F-.
C) Br- is more stable than F- because Br- is less electronegative than F-.
D) Br- is less stable than F- because Br- is less electronegative than F-.
33. Which of the following compounds has the lowest pKa?

A) H2O B) H2S C) NH3 D) CH4
34. Which of the following concepts can be used to explain the difference in acidity
between acetic acid (CH3COOH) and ethanol (CH3CH2OH)?
A) Hybridization B) Electronegativity C) Resonance D) Size
between acetylene (C2H2) and ethylene (C2H4)?
A) Size B) Resonance C) Inductive effect D) Hybridization
between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)?
A) Size B) Inductive effect C) Resonance D) Hybridization
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first.
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
38. Which of the following statements about Lewis acids is true?

A) Lewis acids are proton donors.
B) Lewis acids are proton acceptors.
C) Lewis acids are electron pair donors.
D) Lewis acids are electron pair acceptors.
39. Which of the following statements about Lewis bases is true?

A) Lewis bases are electron pair acceptors.
B) Lewis bases are electron pair donors.
C) Lewis bases are proton donors.
D) Lewis bases are proton acceptors.
40. Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH3OH B) H2O C) CH3COOH D) BF3
41. Which of the following species can be both Lewis acid and Lewis base?
A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III
42. What is the correct classification of the following compound?
CH3-O-CH3
A) Brønsted-Lowry acid and Lewis acid. C) Brønsted-Lowry base.
B) Brønsted-Lowry base and Lewis base. D) Lewis base.
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43. Identify the Lewis acid in the following reaction.
44. Identify the Lewis base in the following reaction.
45. Which of the following compounds is not a Lewis acid?

A) AlCl3 B) HCl C) H2O D) CBr4
46. What is the role of methylchloride (CH3Cl) in the following reaction?
A) Lewis acid C) Brønsted-Lowry acid

B) Lewis base D) Brønsted-Lowry base
47. What is the electrophilic site in the following compounds?
A) I = Carbon; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron.

B) I = Chlorine; II = carbon; III = boron. D) I = Carbon; II = carbon; III = fluorine.
48. What is the nucleophilic site in the following compounds?
A) I = Hydrogen; II =  electrons in bond; III = nitrogen.

B) I = Oxygen; II = carbon; III = nitrogen.
C) I = Hydrogen; II = carbon; III = carbon.
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D) I = Oxygen; II =  electrons in bond; III = nitrogen.
Chapter 3: Intro. to Organic Molecules & Functional Groups
1. Which of the following lists contains common heteroatoms found in organic molecules?
A) N, O, S, P, Cl C) Na, Mg, S, N, Cl
B) Na, O, S, P, Cl D) Na, Mg, O, N, Cl
2. Why do heteroatoms confer reactivity on a particular molecule?

A) Because they have lone pairs and create electron-rich sites on carbon.
B) Because they have lone pairs and create electron-deficient sites on carbon.
C) Because they are electronegative and act as electrophiles.
D) Because they are electropositive and act as nucleophiles.
3. Why do  bonds confer reactivity on a particular molecule?

A) Because  bonds are difficult to break in chemical reactions.
B) Because  bonds make a molecule an acid.
C) Because  bonds are easily broken in chemical reactions.
D) Because  bonds make a molecule an electrophile.
4. Which of the following molecules contain the same functional groups?
A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV
5. Which of the following molecules contain the same functional groups?
A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV
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6. Which of the following molecules are aliphatic hydrocarbons?
A) I, II, III B) I and III C) II, III, IV D) II and IV
7. Which of the following molecules are aromatic hydrocarbons?
A) I B) II C) III D) I and III
8. Which of the following correctly matches the molecules to the names of the functional
groups?
I. CH3OH Carboxylic acid

II. CH3CO2CH3 Ester
III. CH3COCH3 Ketone
IV. H2CO Alcohol
A) I and II B) III and IV C) II and III D) II and IV
groups?
I. CH3OCH3 Ether
II. CH3CONH2 Amine
III. CH3SH Thiol
IV. CH3CHO Alcohol
A) I and II B) II and III C) III and IV D) I and III
groups?
I. CH3NH2 Amide
II. CH3SCH3 Sulfide
III. CH3CONH2 Amine
IV. CH3CO2CH3 Ester
A) I and II B) II and IV C) III and IV D) II and III
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11. Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the
following lists the correct functional groups present in donepezil?
A) Amide, aromatic, ether, ketone. C) Amine, aromatic, ester, ketone.

B) Amide, aromatic, ester, ketone. D) Amine, aromatic, ether, ketone.
12. Consider the molecule atenolol (a  blocker used to treat hypertension). Which of the
following lists the correct functional groups present in atenolol?
A) Primary alcohol, amide, primary amine, aromatic, ether.

B) Secondary alcohol, amide, secondary amine, aromatic, ether.
C) Secondary alcohol, amide, primary amine, aromatic, ether.
D) Secondary alcohol, amide, secondary amine, aromatic, ester.
13. Which of the following structures contains a secondary amine?
14. Which of the following structures contains a primary amine?
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15. Which of the following structures contains an amide?
16. Which of the following structures contains an alkene?
17. Which of the following is a tertiary amine?
18. Which of the following is a secondary alcohol?
19. Which of the following statements best describes the relationship between the surface
area of a molecule and the strength of the intermolecular forces?
A) The larger the surface area, the weaker the intermolecular force.
B) The larger the surface area, the stronger the intermolecular forces.
C) The smaller the surface area, the stronger the intermolecular forces.
D) There is no relationship between surface area and intermolecular forces.
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20. Rank the following compounds in order of increasing strength of intermolecular forces,
putting the molecule with the weakest intermolecular force first.
A) I < II < III B) II < I < III C) I < III < II D) II < III < I
21. Which of the following compounds has the lowest boiling point?
22. Which of the following compounds has the highest boiling point?
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26. Rank the following compounds in order of decreasing boiling point, putting the
compound with the highest boiling point first.
A) I > II > III > IV C) III > II > IV > I

B) III > IV > II > I D) I > IV > II > III
27. Which of the following compounds can form intermolecular hydrogen bonds with a
molecule similar to itself?
28. What is the strongest intermolecular force present in 1-propanol?
A) Ion-ion C) Dipole-dipole
B) Hydrogen bonding D) Induced dipole-induced dipole
29. What intermolecular force is generally considered the strongest?

A) Hydrogen bonding C) Covalent bonds
B) London dispersion forces D) Dipole-dipole
30. What intermolecular force is generally considered the weakest?

A) Hydrogen bonding C) Dipole-dipole
B) London dispersion forces D) Ion-ion
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31. Rank the following compounds in order of increasing melting point, putting the
compound with the least melting point first.
A) II II > III B) II > III > I C) III > II > I D) III > I > II
33. Which of the following intermolecular forces would not form between similar
molecules of the structure below?
A) London dispersion forces C) Hydrogen bonding

B) Ion-ion D) Dipole-dipole
34. Which of the following alkanes is expected to have the highest melting point?
35. Which of the following compounds is expected to be the least soluble in H2O?
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36. Which of the following compounds is expected to be the most soluble in H2O?
37. Which of the following compounds would be expected to be more soluble in hexane
(C6H14)?
38. Which of the following statements about the solubility of organic compounds in H2O is
true?
A) The non-polar part of a molecule that is not attracted to water is said to be
hydrophilic.
B) The non-polar part of a molecule that is not attracted to water is said to be
hydrophobic.
C) The polar part of a molecule that can hydrogen bond to water is said to be
hydrophobic.
D) For an organic compound with one functional group that contains an O or N atom,
the compound is water soluble only if it has  5 carbons.
39. Which of the following compounds is expected to be H2O soluble?
40. What molecular features are required for soap to properly dissolve grease and oil?
A) The molecule must be large.
B) The molecule must contain a polar head.
C) The molecule must contain a non-polar tail.
D) B and C are required.
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41. Which of the following statements about vitamin A, drawn below, are true?
A) Vitamin A is soluble in H2O.

B) Vitamin A is insoluble in organic solvents.
C) Vitamin A contains an aromatic ring.
D) Vitamin A is insoluble in H2O.
42. Which of the following statements about vitamin C, drawn below, are true?
A) Vitamin C is insoluble in H2O.

B) Vitamin C is soluble in H2O.
C) Vitamin C is an aliphatic hydrocarbon.
D) Vitamin C contains a ketone functional group.
43. Which of the following could most likely serve as an ionophore?
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44. The indicated carbon atom is:
A) Electrophilic because it is electron-deficient.

B) Nucleophilic because it is electron-deficient.
C) Electrophilic because it is electron-rich.
D) Nucleophilic because it is electron-rich.
45. The indicated bond is:
A) Nucleophilic because it is electron-deficient.

B) Electrophilic because it is electron-deficient.
C) Nucleophilic because it electron-rich.
D) Electrophilic because it is electron-rich.
46. The indicated bond is:
A) Nucleophilic because it is electron-deficient.

B) Electrophilic because it is electron-rich.
C) Nucleophilic because it is electron-rich.
D) Electrophilic because it is electron-deficient.
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47. Which of the following list the correct functional groups found in aspartame, the
artificial sweetener?
A) Amine, aromatic, carboxylic acid, ether, ketone.

B) Amine, amide, aromatic, carboxylic acid, ester.
C) Amide, alcohol, aromatic, carboxylic acid, ether.
D) Amine, aromatic, carboxylic acid, ester, nitrile.
48. Rank the following compounds in order of decreasing boiling point, putting the
A) I > III > IV > II C) IV > I > II > III

B) IV > II > I > III D) I > IV > II > III
Chapter 4: Alkanes
1. Which of the following statements about alkanes is not true?

A) Alkanes are aliphatic hydrocarbons.
B) Alkanes contain only C-C and C-H  bonds.
C) Alkanes are acyclic or cyclic.
D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number
of carbons.
2. Which of the following statements about alkanes is true?

A) Alkanes are aliphatic hydrocarbons having only C-C and C-H  bonds.
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B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number
of carbons.
C) Acyclic alkanes contain carbons joined in one or more rings.
D) Acyclic alkanes have general molecular formula CnH2n.
3. What is the molecular formula of an alkane that has twenty-three carbon atoms?
A) C23H46 B) C23H48 C) C23H50 D) C23H44
4. What is the molecular formula of a cycloalkane that has six carbon atoms?
A) C6H14 B) C6H10 C) C6H12 D) C6H16
5. What is the approximate C-C-C bond angle in propane?

A) 90° B) 109.5° C) 120° D) 180°
6. What is the hybridization of a carbon atom in an alkane?

7. How many constitutional isomers are there with the molecular formula C5H12?
A) 2 B) 3 C) 4 D) 5
8. How many constitutional isomers are there with the molecular formula C6H14?
A) 2 B) 3 C) 4 D) 5
9. Which of the following is not another representation for 2-methylbutane?
10. Which of the following compounds has primary, secondary, tertiary and quaternary
carbon atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
11. Which of the following compounds has only primary and secondary carbon atoms?
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12. Which of the following compounds has only primary, secondary and tertiary carbon
atoms?
13. Which of the following compounds has only primary, secondary and quaternary carbon
atoms?
14. Which of the following compounds has primary, secondary and tertiary hydrogen
atoms?
A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane
15. Which of the following compounds has only primary and secondary hydrogen atoms?
A) 2-Methylpentane C) 3-Methylpentane
B) 2,2,3-Trimethylpentane D) 2,2-Dimethylpentane
16. How many cycloalkane constitutional isomers (excluding stereoisomers) are there with
molecular formula C5H10?
A) 2 B) 3 C) 4 D) 5
17. What is the parent chain for the following compound?
A) Hexane B) Heptane C) Octane D) Nonane
18. What is the parent chain for the following compound?
A) Heptane B) Octane C) Nonane D) Decane
19. What is the name of the alkyl group that contains two carbons in a straight chain and
one-carbon branch?
A) Ethyl B) Propyl C) Isopropyl D) None of the above
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20. What is the IUPAC name for the following compound?
A) 4-Ethyl-5-methyloctane C) 4-Methyl-3-propylheptane
B) 4-Methyl-5-ethyloctane D) 4-Methyl-5-propyloctane
A) 3,5-Diethyl-6-methylheptane C) 3-Ethyl-5-isopropylheptane
B) 3,5-Diethyl-2-methylheptane D) 5-Ethyl-3-isopropylheptane
A) 2,3-Dimethyl-4-sec-butylheptane C) 3,5,6-Trimethyl-4-propylheptane
B) 4-sec-Butyl-2,3-dimethylheptane D) 2,3,5-Trimethyl-4-propylheptane
A) 5-Ethyl-3,6-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane
B) 3-Ethyl-2,5-dimethylheptane D) 5-Ethyl-3,6-dimethyloctane
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A) 2,3,5-Trimethylhexane C) 2,4-Diethyl-5-methylheptane
B) 2,4,5-Triethylhexane D) 4-Ethyl-3,6-dimethyloctane
A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane
B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane
C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane
D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane
A) 3-Ethyl-1-methylcyclohexane C) 1-Ethyl-3-methylhexane
B) 1-Ethyl-3-methylcyclohexane D) 3-Ethyl-1-methylhexane
A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane
B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane
C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane
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D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane
A) 1,4-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane
B) 1,3-Dimethylcyclohexane D) 1,4-Dimethylcyclopentane
A) 1-Butylcyclohexane C) 1-Cyclohexylbutane
B) Cyclohexanebutane D) Butylcyclohexane
A) Hexylcyclopentane C) 1-Cyclopentylhexane
B) 1-Hexylcyclopentane D) 1-Cyclopentylheptane
A) 1-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane
B) 1-sec-Butyl-3-methylcyclohexane D) 1-sec-Butyl-3-methylhexane
32. What is the common name of the following alkyl group?
A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl
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33. What is the common name of the following alkyl group?
A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl
34. Rank the following alkanes in order of decreasing boiling point, putting the alkane with
the highest boiling point first.
A) I > II > III B) I > III > II C) II > III > I D) III > II > I
35. Rank the following alkanes in order of increasing melting point, putting the alkane with
the lowest melting point first.
A) I < III < II B) I < II < III C) II < III < I D) III < II < I
36. Which of the following statements about the conformations of acyclic alkanes is true?
A) Conformations are the same arrangements of atoms that cannot be interconverted
by rotation about single bonds.
B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond
angle on the adjacent carbon.
C) In the staggered conformation, the C-H bonds on one carbon are directly aligned
with the C-H bonds on the adjacent carbon.
D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a
staggered conformation, and vice versa.
37. Which of the following statements about the conformations of acyclic alkanes is not
true?
A) The staggered and eclipsed conformations are equally stable.
B) The staggered conformations are more stable than the eclipsed conformations.
C) An energy minimum and maximum occur every 60° as the conformation changes
from staggered to eclipsed.
D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
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38. Which of the following statements about the conformations of acyclic alkanes is true?
A) A staggered conformation with two larger groups 180° from each other is called
gauche.
B) Staggered conformations are at energy maxima and eclipsed conformations are
energy minima.
C) A staggered conformation with two larger groups 60° from each other is called
anti.
D) Gauche conformations are generally higher in energy than anti conformations.
39. Which of the following is not a conformer of butane?
40. Which of the following are gauche conformers?
A) I and II B) I and III C) II and IV D) II and III
41. Which of the following are anti conformers?
A) I and II B) II and III C) I and IV D) II and IV
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42. Which of the following conformers has the highest energy?
43. Rank the conformers of butane in order of decreasing stability, putting the most stable
first.
A) IV > I > II > III C) II > III > I > IV

B) IV > I > III > II D) I > IV > II > III
44. Which of the following is the highest energy conformer of 2,3-dimethylbutane?
45. Which of the following is the lowest energy conformer of 2,3-dimethybutane?
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46. Which of the following cycloalkanes has the most angle strain?
A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
47. Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane
48. Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?
49. Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?
50. Which of the following is the most stable conformation of cis-1-ethyl-3-

isopropylcyclohexane?
51. Which of the following is the most stable conformation of trans-1-isopropyl-3-

methylcyclohexane?
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52. Select the most stable conformer of cis-1,3-cyclohexanediol.
53. What is the alternate chair conformation of the following compound?
54. Which of the following is the most stable conformation of the following compound?
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55. Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability,

putting the most stable first.
A) I > II > III > IV C) III > IV > II > I

B) III > II > IV > I D) I > II > IV > III
56. What are the products of the combustion of alkanes?

A) Carbon and hydrogen C) Carbon dioxide and hydrogen
B) Carbon and water D) Carbon dioxide and water
Chapter 5: Stereochemistry
1. What is the main carbohydrate in the seeds and roots of plants?

A) Starch B) Glucose C) Cellulose D) Glycogen
2. Which of the following statements about starch and cellulose is true?

A) Starch and cellulose are not stereoisomers.
B) In cellulose, the O atom joins two rings using one equatorial and one axial bond.
C) In starch, the O atom joins two rings using two equatorial bonds.
D) In cellulose, the O atom joins two rings using two equatorial bonds.
3. Which of the following statements about constitutional isomers if not true?

A) They have different IUPAC names.
B) They always have the same functional groups.
C) They have different physical properties.
D) They have different chemical properties.
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4. Which of the following statements about stereoisomers is not true?

A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans.
B) Stereoisomers differ in configuration.
C) Stereoisomers always have the same functional groups.
D) Stereoisomers differ only in their structural formula.
5. What is the relationship between the following two compounds?
A) Stereoisomers C) Identical
B) Constitutional isomers D) Not isomers, different compounds
A) Constitutional isomers C) Stereoisomers

B) Identical D) Not isomers, different compounds
A) Constitutional isomers C) Stereoisomers

B) Identical D) Not isomers, different compounds
A) Constitutional isomers C) Identical

B) Stereoisomers D) Not isomers, different compounds
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9. Which of the following is the definition of chirality?

A) The existence of a molecule with a mirror image.
B) The existence of a molecule with a carbon atom that has four different substituents.
C) The existence of a molecule that is superimposable on its mirror image.
D) The existence of a molecule that is not superimposable on its mirror image.
10. Which of the following statements is not true?

A) A molecule that is superimposable on its mirror image is said to achiral.
B) A molecule that is not superimposable on its mirror image is said to be chiral.
C) A molecule that is superimposable on its mirror image is said to be chiral.
D) A carbon atom bonded to four different groups is a stereogenic center.
11. Which of the following statements is true?

A) Enantiomers are mirror images that are not superimposable.
B) A molecule that is superimposable on its mirror image is chiral.
C) A chiral molecule usually contains a plane of symmetry.
D) An achiral molecule does not contain a plane of symmetry.

A) Achiral molecules usually contain a plane of symmetry.
B) With one tetrahedral stereogenic center, a molecule may or may not be chiral.
C) With two or more stereogenic centers, a molecule is always chiral.
D) Chiral molecules usually contain a plane of symmetry.
13. Which of the following is the correct definition for a pair of enantiomers?
A) A pair of stereoisomers that have a plane of symmetry.
B) A pair of stereoisomers that are not mirror images of each other.
C) A pair of stereoisomers that are not superimposable mirror images of each other.
D) A pair of stereoisomers that are superimposable mirror images of each other.
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14. Which of the following molecules has a plane of symmetry?

A) The presence of a plane of symmetry makes a molecule chiral.
B) An achiral molecule must have one or more stereogenic centers.
C) All molecules that have stereogenic centers are chiral.
D) Stereoisomers that are not superimposable on their mirror image are enantiomers.
16. Which of the following molecules are chiral?
I. cis-1,3-Dibromocyclohexane
II. 1-Bromo-1-methylcyclohexane
III. trans-1-Bromo-3-methylcyclohexane
IV. cis-1-Bromo-3-methylcyclohexane
A) I, II B) II, III C) I, IV D) III, IV
I. 2-Chlorobutane
II. 3-Bromopentane
III. 1-Bromo-2-methylpropene
IV. 2-Bromo-3-methylbutane
A) I, II B) I, IV C) II, III D) III, IV
18. Which of the following molecules are achiral?
A) II, III B) I, II C) I, IV D) III, IV
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A) II, III B) I, II C) I, IV D) III, IV
20. How many stereogenic centers are present in ephedrine, a bronchodilator and
decongestant?
A) 0 B) 1 C) 2 D) 3
21. How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
22. How many stereogenic centers are present in fructose, a simple sugar?
A) 1 B) 2 C) 3 D) 4
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A) 1 B) 2 C) 3 D) 4
24. How many stereogenic centers are present in menthol?
A) 1 B) 2 C) 3 D) 4
A) 1 B) 2 C) 3 D) 4
26. How many stereogenic centers are present in the following molecule?
A) 1 B) 2 C) 4 D) 5
27. How many stereoisomers are possible for a molecule with formula
CH3CHBrCH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
28. How many stereoisomers can be drawn for a molecule with formula
CH3CH(OH)CH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
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29. What is the total number of possible stereoisomers for the following molecule?
A) 2 B) 4 C) 6 D) 8
30. How many isomers can be drawn (constitutional and stereoisomers) for
dimethycyclopropane?
A) 2 B) 3 C) 4 D) 6
31. How many chiral stereoisomers can be drawn for dimethycyclopropane?

A) 1 B) 2 C) 3 D) 4
32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures
and certain types of chronic pain?
A) 0 B) 1 C) 2 D) 3
A) 0 B) 1 C) 2 D) 3
34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
A) III > I > II > IV C) III > II > IV > I

B) I > II > IV > III D) III > IV > II > I
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Prelog system.
A) I > II > III > IV C) II > I > III > IV

B) II > I > IV > III D) I > II > IV > III
Prelog system.
A) I > III > IV > II C) IV > III > I > II

B) III > IV > I > II D) IV > I > III > II
Prelog system.
A) I > II > IV > III C) IV > I > II > III

B) IV > II > I > III D) III > II > I> IV
Prelog system.
A) IV > III > I > II C) III > IV > I > II

B) IV > I > III > II D) II > I > III > IV
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39. Which of the following compounds has a plane of symmetry?
A) I and II B) II and III C) II, III and IV D) III and IV
40. Which of the following structures has a different configuration from the other three?
41. Which of the following structures has a different configuration from the other three?
42. Which of the following structures has the S configuration?
A) Only I B) Only II C) Only I and II D) I, II and III
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43. Which of the following structures has the R configuration?
44. Which of the following structures has the R configuration?
45. Which of the following is the definition for a pair of diastereomers?

A) A pair of stereoisomers with stereogenic centers which is not chiral.
B) A pair of stereoisomers that are superimposable mirror images of each other.
C) A pair of stereoisomers that are not superimposable mirror images of each other.
D) A pair of stereoisomers that are not mirror images of each other.
46. What is the relationship between the following compounds?
A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical
Page 51
Page 52
54. Which of the following statements about meso compounds is not true?
A) A meso compound generally has a plane of symmetry.
B) A meso compound and its mirror image are identical.
C) A meso compound is achiral.
D) A meso compound is chiral.
55. Which of the following compounds is a meso compound?

A) (2R, 3S)-dichlorobutane C) (2R, 3S)-3-chloro-2-butanol
B) (2R, 3R)-dichlorobutane D) (2R, 3R)-3-chloro-2-butanol
56. Which of the following compounds are meso?
A) Only I B) Only II C) I and II D) Neither
57. Which of the following compounds can have a meso stereoisomer?
58. How many stereoisomers of 1,3-dibromocyclopentane exist?

A) 1 B) 2 C) 3 D) 4
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59. Which of the following compounds does not have a plane of symmetry?
A) Only I and II B) Only II C) Only III and IV D) Only I, II and IV
60. Which of the following cyclic molecules is a meso compound?
61. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
A) 3 B) 4 C) 5 D) 6
62. A natural product was isolated in the laboratory, and its observed rotation was +10°
when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O.
What is the specific rotation of this compound?
A) -10° B) +100° C) +10° D) -100°
63. A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates

plane polarized light by +4°. What is the specific rotation of the S enantiomer?
A) +50° B) -40° C) +40° D) -50°
64. How much of the R enantiomer is present in 10 g of a mixture which has an

enantiomeric excess of 30% of the S isomer?
A) 3.0 g B) 3.5 g C) 6.5 g D) 7.0 g
65. A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates

plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of
the S enantiomer in the same polarimeter.
A) +5.6° B) +11.2° C) +2.8° D) +1.4°
66. What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the
other?
A) 70 B) 85 C) 40 D) 30
67. If a mixture has an ee of 90%, what is the percentage of each enantiomer?

A) 65% : 35% B) 55% : 45% C) 80% : 20% D) 95% : 5%
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68. A reaction mixture is three parts of one enantiomer and one part of the other. What is
the percent ee of this mixture?
A) 75 B) 40 C) 65 D) 50
Chapter 6: Understanding Organic Reactions
1. Which of the following statements about substitution reactions is true?

A) Substitution reactions involve  bonds.
B) Substitution reactions involve  bonds.
C) One  bond breaks and another forms at a different carbon atom.
D) One  bond breaks and another forms at the same carbon atom.
2. What kind of reaction does the conversion of A to B represent?
A) Addition reaction. C) Elimination reaction.

B) Substitution reaction. D) Acid-base reaction.
3. Which of the following statements about elimination reactions is true?

A) Two  bonds are broken. C) Two  bonds are broken.
B) Two  bonds are formed. D) Two  bonds are formed.
A) Addition reaction. C) Substitution reaction.

B) Elimination reaction. D) Oxidation-reduction reaction.
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5. Which of the following statements about addition reactions is true?

A) Two  bonds are formed. C) Two  bonds are formed.
B) Two  bonds are broken. D) One  bond is formed.
A) Acid-base reaction. C) Substitution reaction.

B) Elimination reaction. D) Addition reaction.
7. Which of the following statements about bond breaking is true?

A) Homolysis and heterolysis require energy.
B) In homolysis, the electrons in the bond are divided unequally.
C) In heterolysis, the electrons in the bond are divided equally.
D) Homolysis generates charged intermediates.
8. Which of the following statements about bond breaking is not true?

A) Homolysis generates uncharged reactive intermediates with unpaired electrons.
B) Homolysis require energy but heterolysis does not require energy.
C) Heterolysis generates charged intermediates.
D) Heterolysis involves unequal sharing of bonding electrons by atoms.

A) Ionic intermediates are formed in radical reactions.
B) Radicals are intermediates in polar reactions.
C) Carbocations are electrophiles.
D) Radicals are nucleophiles.

A) In polar reactions, a nucleophile reacts with an electrophile.
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B) Carbocations are electrophiles.

C) Carbanions are nucleophiles.
D) A half-headed curved arrow shows the movement of an electron pair.

A) Bond breaking is endothermic.
B) The bond dissociation energy for bond breaking is always negative.
C) Bond making is exothermic.
D) The bond dissociation energy for bond formation is always negative.

A) Bond dissociation energies increase down a column of the periodic table.
B) When H° is positive, more energy is released in forming bonds than is needed to
break bonds.
C) When H° is negative, more energy is needed to break bonds than is released in
forming bonds.
D) Bond dissociation energies decrease down a column of the periodic table.
13. Using the bond dissociation energies given, calculate H° for the following reaction.
Bond A-B  H° KJ/mol

(CH3)3C-Cl 331
H-OH 498
(CH3)3C-OH 401
H-Cl 431
A) +3 KJ/mol B) -3 KJ/mol C) -67 KJ/mol D) +70 KJ/mol
14. Using the bond dissociation energies given, calculate H° for the following reaction.
Bond A-B  H° KJ/mol

CH3CH2-Br 285
H-OH 498
CH3CH2-OH 393
H-Br 368
A) +108 KJ/mol B) -130 KJ/mol C) -22 KJ/mol D) +22 KJ/mol
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15. Which of the following statements about the equilibrium constant, Keq, is true?
A) When Keq > 1, the equilibrium favors the reactants.
B) When Keq < 1, the equilibrium favors the products.
C) The size of Keq tells about the position of equilibrium.
D) For a reaction to be useful, the equilibrium must favor the reactants.
16. Which of the following statements about equilibrium is true?

A) Equilibrium favors the products when the energy of the products is higher than the
energy of the reactants.
B) Equilibrium favors the reactants when the energy of the product is lower than the
energy of the reactants.
C) Equilibrium favors the products when they are less stable than the starting material
of a reaction
D) Equilibrium favors the products when they are more stable than the starting
material of a reaction.
17. Which of the following expressions summarizes the correct relationship between the
free energy change, G°, and the equilibrium constant, Keq?
A) Keq > 1 when G° > 0 C) Keq < 1 when G° < 0
B) Keq > 1 when G° < 0 D) Keq < 1 when G° = 0
18. Which of the Keq corresponds to the lowest value of G°?

A) Keq = 10-3 B) Keq = 10-2 C) Keq = 10-1 D) G° cannot be determined
19. Which of the Keq corresponds to the highest value of G°?

A) Keq = 10-1 B) Keq = 10-2 C) Keq = 10-3 D) Keq = 10-5
20. Which of the Keq corresponds to the most negative value of G°?
A) Keq = 1 B) Keq = 101 C) Keq = 102 D) Keq = 103

A) The product is favored in reaction in which H° is a positive value.
B) Entropy decreases when an acyclic compound forms a ring.
C) In homolytic bond cleavage, entropy decreases and favors formation of products.
D) The starting material is favored in a reaction in which H° is a negative value.
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A) The size of the activation energy tells us about the reaction mechanism.
B) The size of the activation energy tells us about the reaction rate.
C) A slow reaction has low activation energy.
D) A fast reaction has large activation energy.

A) Two reactions can have identical values for H° but very different Ea values.
B) The larger the activation energy, the slower the reaction.
C) H° determines the height of the energy barrier.
D) The lower the activation energy, the faster the reaction.
24. What is the name given to the reaction species that lies at an energy minimum between
steps on a reaction energy diagram?
A) Transition state C) Reactive intermediate
B) Activation energy D) Equilibrium product
25. Which of the following statements about a two-step reaction mechanism is true?
A) The transition states are located at energy minima.
B) Each step is characterized by its own value of H° and Ea.
C) The rate-determining step has the lower energy transition state.
D) The reactive intermediate is located at an energy maximum.
26. Which reaction is fast and has Keq= 1?
A) A B) B C) C
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27. Which reaction has a positive G°, assuming that entropy changes are negligible
compared to enthalpy changes?
A) A B) B C) C
28. Which reaction is slowest?
A) A B) B C) C
29. In which reaction is Keq > 1?
A) A B) B C) C
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30. How many transition states are present in the reaction in the energy diagram?
A) 0 B) 1 C) 2 D) 3
31. Which of the following letters represents H° for the forward reaction in the following
energy diagram?
A) A B) B C) C D) D
32. How many transition states and intermediates would the reaction profile have for the
reaction shown below?
A) Three transition states and three intermediates

B) Two transition states and two intermediates
C) Three transition states and two intermediates
D) Two transition states and three intermediates
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33. Which step would most likely have the largest energy of activation?
A) Step one
B) Step two
C) Step three
D) It cannot be determined from the information provided
34. A decrease in which of the following results in an increase in the rate of a chemical
reaction?
A) Energy of activation B) Concentration C) Temperature D) Kinetic energy
35. Which of the following reaction quantities will have an effect on reaction rate?
A) G° B) H° C) Keq D) Ea

A) Fast reactions have small rate constants.
B) Slow reactions have large rate constants.
C) A rate equation contains concentration terms for all reactants involved in a one-step
mechanism.
D) A rate equation contains concentration terms for all the reactants involved in a
multi-step reaction.
37. The equilibrium constant for the conversion of A to D is predicted to be which of the
following?
A) Keq = 1
B) Keq < 1
C) Keq > 1
D) Cannot be determined from the information provided
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38. The G° (free energy change) for the conversion of A to B is predicted to be which of
the following?
A) G° = 0
B) G° < 0
C) G° > 0
D) Cannot be determined from the information provided
39. What kind of reaction does the conversion of A to D represent?
A) Addition reaction C) Elimination reaction

B) Substitution reaction D) Oxidation-reduction reaction
40. If the conversion of A to B is slow and B to C is fast, what is the rate equation for this
reaction?
A) Rate = k[(CH3)2CHCl][H2O] C) Rate = k[(CH3)2CH]+[H2O]

B) Rate = k[(CH3)2CHCl] D) Rate = k[(CH3)2CH]+
41. Which compound would you predict to be highest in energy?
A) A B) B C) C D) D
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42. Calculate Ea for the conversion of C  B.
Ea (A  B) = +10 kcal
Ea (B  C) = +4 kcal
H (A  B) = +8 kcal
H (B  C) = -5 kcal
A) +3 kcal B) +7 kcal C) +9 kcal D) None of the above
43. The following is an energy diagram for the conversion of A  B  C. The energies of
activation and H's for each step are also given. Calculate H overall as shown on the
energy diagram for A  B  C.
Ea (A  B) = +10 kcal
Ea (B  C) = +4 kcal
H (A  B) = +8 kcal
H (B  C) = -5 kcal
A) +3 kcal B) +7 kcal C) +9 kcal D) None of the above
44. Which of the following statements about a catalyst is true?

A) A catalyst accelerates a reaction by changing the amount of reactant and product at
equilibrium.
B) A catalyst accelerates a reaction by lowering the energy of activation.
C) A catalyst accelerates a reaction by raising the energy of activation.
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D) A catalyst accelerates a reaction by lowering the equilibrium constant.
45. Which of the following statements about enzymes is true?

A) Enzymes increase the activation energy for a reaction.
B) Enzymes decrease the equilibrium constant.
C) Enzymes shift the equilibrium to favor the product.
D) Enzymes lower the transition state for the rate-determining step.
Chapter 7: Alkyl Halides and Nucleophilic Substitution
1. Which of the following alkyl halides is a primary alkyl halide?
2. Which of the following alkyl halides is a secondary alkyl halide?
3. Which of the following alkyl halides is a tertiary alkyl halide?
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4. Which of the following alkyl halides is a vinyl alkyl halide?
5. Which of the following structures have the correct common name?
A) I and II B) II and IV C) II and III D) III and IV
A) I and II B) II and III C) I and III D) III and IV
A) I and II B) II and III C) II and IV D) III and IV
8. What is the IUPAC name of the following compound?
A) 2-Methyl-4-chloropentane C) 2-Chloro-1-isopropylpropane
B) 2-Chloro-4-methylpentane D) 2-Chloro-2-methylpentane
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A) 2-Bromo-5-methyloctane C) 2-Bromo-5-methylheptane
B) 2-Bromo-3-methylheptane D) 6-Bromo-3-methylheptane
A) 2-Bromo-5,5-dimethylheptane C) 6-Bromo-3,3-dimethylheptane
B) 3,3-Dimethyl-6-bromoheptane D) 2-Bromo-5,5-dimethyloctane
A) 2-Chloro-4-isopropyl-2,6-dimethyloctane
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane
A) (R)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane
B) (S)-3-Chloro-6-ethyloctane D) (R)-6-Chloro-3-ethyloctane
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A) trans-4-Methylcyclohexyl chloride C) trans-4-Methyl-1-chlorocyclohexane

B) trans-p-Chloromethylcyclohexane D) trans-1-Chloro-4-methylcyclohexane
A) (R)-3-Bromo-1-methylcyclohexene C) (S)-1-Bromo-3-methyl-2-cyclohexene
B) (S)-3-Bromo-1-methylcyclohexene D) (R)-1-Bromo-3-methyl-2-cyclohexene
A) (E)-2-Bromo-3,4-dimethyl-2-pentene
B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene
C) (Z)-2-Bromo-3,4-dimethyl-2-pentene
D) (E)-1-Bromo-1,2,3-trimethyl-1-butene
16. Rank the following halides in order of decreasing polarity, putting the most polar first.
A) II > IV > I > III C) I > II > III > IV

B) IV > II > I > III D) IV > III > II > I
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17. Rank the following molecules in order of increasing polarity, putting the least polar first.
A) IV < III < II < I C) I < II < III < IV

B) I < IV < III < II D) II < I < III < IV
18. Which of the following statements about the reactions of alkyl halides is true?
A) The characteristic reactions of alkyl halides are addition and elimination.
B) The characteristic reactions of alkyl halides are addition and substitution.
C) The characteristic reactions of alkyl halides are elimination and substitution.
D) The characteristic reactions of alkyl halides are oxidation and reduction.

A) All good leaving groups are strong bases with weak conjugate acids.
B) Left-to-right across a row of the periodic table, leaving group ability decreases.
C) Down a column of the periodic table, leaving group ability decreases.
D) The conjugate bases of strong acids are good leaving groups.
20. Rank the following in order of decreasing leaving group ability, putting the best first.
A) III > II > IV > I C) IV > I > II > III

B) III > II > I > IV D) II > III > I > IV

A) All good leaving groups are weak bases with strong conjugate acids.
B) Left-to-right across a row of the periodic table, leaving group ability increases.
C) Down a column of the periodic table, leaving group ability increases.
D) Equilibrium favors the products of the nucleophilic substitution when the leaving
group is a stronger base than the nucleophile.
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22. Rank the following in order of increasing leaving group ability, putting the worst
leaving group first.
A) IV < II < III < I C) II < IV < I < III

B) III < IV < I < II D) I < III < II < IV

A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide.
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases.
C) Sterically hindered bases are also called nonnucleophilic bases.
D) Steric hindrance decreases basicity but not nucleophilicity.

A) In polar protic solvents, nucleophilicity decreases down a column of the periodic
table as the size of the anion increases.
B) Nucleophilicity is affected by the solvent used in a substitution reaction.
C) Polar protic solvents are capable of intermolecular hydrogen bonding.
D) Polar protic solvents solvate both cations and anions.
25. Which of the following solvents is not a polar protic solvent?
26. Rank the following ions in order of increasing nucleophlicity in polar protic solvents,
starting with the least nucleophilic ion.
A) I < II < III < IV C) I < II < IV < III
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B) IV < III < II < I D) IV < III < I < II
27. Which of the following anions is the most nucleophilic in polar aprotic solvents?
A) F- B) Cl- C) Br- D) I-
28. Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic
first.
A) II > III > I > IV C) II > III > IV > I

B) III > II > IV > I D) III > II > I > IV
29. Which of the following is the most nucleophilic?

A) CH4 B) H2O C) NH3 D) HF
30. Rank the following in order of increasing nucleophilicity, putting the least nucleophilic
first.
A) II < IV < I < III C) III < IV < I < II

B) IV < III < II < I D) II < I < IV < III
31. The reaction of bromoethane with sodium acetate affords the substitution product
methyl acetate. What is the effect of doubling the concentration of sodium acetate on
the rate of the reaction?
A) The rate remains the same. C) The rate increases by a factor of 2.
B) The rate decreases by a factor of 2. D) The rate increases by a factor of 4.
32. The reaction of 1-bromobutane with sodium hydroxide affords the substitution product
1-butanol. What would happen to the rate of the reaction if the concentration of both 1-
bromobutane and sodium hydroxide were doubled?
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33. The reaction of tert-butyl bromide, (CH3)3CBr, with ethanol affords the substitution
product tert-butyl ethyl ether, (CH3)3COCH2CH3, in acidic conditions. What would
happen to the rate of the reaction if the concentration of ethanol was doubled?
34. Which of the following statements about SN2 reactions is true?

A) The rate of reaction is dependent on just the substrate.
B) The fastest reaction will occur with a tertiary alkyl halide.
C) The mechanism is a two-step process.
D) Displacement occurs with inversion of configuration.
35. Which of the following statements about the SN2 mechanism for nucleophilic
substitution reactions is true?
A) Involves one step and occurs with retention of configuration.
B) Involves two steps and occurs with inversion of configuration.
C) Involves one step and occurs with inversion of configuration.
D) Involves one step and occurs with racemization.
36. Which compound is most likely to follow second-order kinetics in a substitution

reaction?
A) CH3Br B) (CH3)3CCH2Br C) CH3CH2Br D) (CH3)2CHBr
37. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium
hydroxide?
A) 1-Iodobutane
B) 1-Chlorobutane
C) 1-Fluorobutane
D) 1-Bromobutane
38. Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive
first.
A) I > II > III B) II > I > III C) III > I > II D) I > III > II
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39. Given the following substitution reaction, what would the effect be of changing the
solvent from CH3OH to (CH3)2S=O?
CH3(CH2)5Br + NaOH  CH3(CH2)5OH + Br-

A) The rate would decrease because SN1 reactions are favored by polar protic solvents.
B) The rate would increase because SN2 reactions are favored by polar aprotic
solvents.
C) The rate would increase because SN1 reactions are favored by polar protic solvents.
D) The rate would decrease because SN2 reactions are favored by polar aprotic
solvents.
40. Which of the following is a polar aprotic solvent?
41. Which of the following statements about an SN1 reaction mechanism is true?
A) The reaction is fastest with primary alkyl halide.
B) The reaction exhibits a one-step mechanism.
C) The reaction rate increases as the leaving group ability increases.
D) The reaction rate increases as the strength of the nucleophile increases.
42. Which of the following statements about an SN1 reaction mechanism is true?
A) The reaction involves two steps and occurs fastest with primary alkyl halides.
B) The reaction involves one step and occurs fastest with primary alkyl halides.
C) The reaction involves one step and occurs fastest with tertiary alkyl halides.
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.
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43. Which of the following alkyl halides will react fastest with CH3OH in an SN1
mechanism?
44. What is the rate-determining step of an SN1 reaction mechanism?

A) Reaction of the nucleophile with the carbocation to form the product.
B) Breaking the bond between the carbon and the leaving group to generate a
carbocation.
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon.
D) None of the above.
45. Which of the following rate laws describes the kinetics of an SN1 reaction?
A) Rate = k[alkyl halide] C) Rate = k[nucleophile]
B) Rate = k[alkyl halide][nucleophile] D) Rate = k[solvent]
46. Which of the following carbocations is the most stable?
47. Rank the following carbocations in order of decreasing stability, putting the most stable
first.
A) I > II > III B) II > I > III C) III > I > II D) III > II > I
48. Which of the following is not a characteristic of an SN1 reaction?

A) The rate is proportional to the concentration of substrate.
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B) The reaction is favored in polar protic solvents.

C) The rate is independent of the concentration of the nucleophile.
D) The electrophilic carbon undergoes inversion of stereochemistry.
49. Which of the following statements about carbocation stability is true?

A) Carbocations are stabilized by electron-withdrawing inductive effects only.
B) Carbocations are stabilized by electron-withdrawing inductive effects and
hyperconjugation.
C) Carbocations are stabilized by electron-donating inductive effects only.
D) Carbocations are stabilized by electro-donating inductive effects and
hyperconjugation.
50. Which of the following statements about the Hammond postulate is not true?
A) The Hammond postulate provides a quantitative estimate of the energy of a
transition state.
B) In endothermic reactions, the transition state is closer in energy to the products.
C) In exothermic reactions, the transition state is closer in energy to the reactants.
D) The Hammond postulate provides a qualitative estimate of the energy of a
transition state.
51. Which of the following statements about the Hammond postulate is true?
A) In an exothermic reaction, lowering the energy of the transition state increases the
activation energy, Ea.
B) In an endothermic reaction, the more stable product forms faster.
C) In an endothermic reaction, the less stable product forms faster.
D) In an endothermic reaction, the activation energy, Ea, is similar for both products.
52. The reaction of what nucleophile and substrate is represented by the following transition
state?
A) Methanol with 2-bromopropane C) Methoxide with 1-bromopropane

B) Methoxide with 2-bromopropane D) Methanol with 1-bromopropane
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53. For the following reaction, use the identity of the alkyl halide and nucleophile to
determine which substitution mechanism occurs. Then determine which solvent affords
the faster reaction.
A) SN1, CH3OH B) SN1, DMSO C) SN2, CH3OH D) SN2, DMSO
A) SN1, H2O B) SN1, DMF C) SN2, H2O D) SN2, DMF
A) SN1, CH3OH B) SN1, HMPA C) SN2, CH3OH D) SN2, HMPA
56. What is the product of the nucleophilic substitution reaction shown below?
A) Only I B) Only II C) I and II D) None
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62. What is the starting material in the reaction shown below?
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63. What is the starting material in the reaction shown below?
64. Which of the following statements explain why aryl halides and vinyl halides do not
undergo nucleophilic substitution by either the SN1 or SN2 mechanism?
A) They don't undergo SN1 reactions because a higher percent s-character makes the
bond longer and stronger.
B) They don't undergo SN2 reactions because a higher percent s-character makes the
bond shorter and stronger.
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a
highly unstable carbocation.
D) They don't undergo SN1 reactions because the carbocation is highly electronegative.
Chapter 8: Alkyl Halides and Elimination Reactions
1. Which of the following statements about an E1 mechanism is not true?

A) It is a two-step process and has the same first step as an SN1 mechanism.
B) It involves the formation of a carbocation from eliminating a good leaving group.
C) A common competing reaction is rearrangement of a less stable carbocation to a
more stable carbocation.
D) The loss of a proton by the carbocation is a slow step.
2. How many unique  carbons are found in the alkyl halide below?
A) 1 B) 2 C) 3 D) 4
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3. How many unique  carbons are found in the alkyl halide below?
A) 1 B) 2 C) 3 D) 4
4. Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents
bonded to the double bond.
A) I = Disubstituted; II = trisubstituted; III = trisubstituted.

B) I = Monosubstituted; II = disubstituted; III = trisubstituted.
C) I = Disubstituted; II = disubstituted; III = trisubstituted.
D) I = Disubstituted; II = trisubstituted; III = disubstituted.
5. Which of the following represents the rate law for an E2 reaction?

A) Rate = k[alkyl halide] C) Rate = k[alkyl halide]2
B) Rate = k[alkyl halide][base] D) Rate = k[base]2
6. Which of the following statements about the mechanism of an E2 reaction is true?

A) All bonds are broken and formed in multiple steps.
B) The reaction is not concerted.
C) Entropy favors the reactants of an E2 reaction.
D) Entropy favors the products of an E2 reaction.
7. How many different E2 products can form from the dehydrohalogenation of 2-

bromobutane?
A) 1 B) 2 C) 3 D) 4
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8. What is the major elimination product in the reaction of 1-bromobutane with potassium
tert-butoxide in tert-butanol?
A) cis-2-Butene B) 1-Butene C) trans-2-Butene D) Butanol
9. What is the major product of the following reaction?
10. Which of the following statements about the mechanism of an E2 reaction is not true?
A) It is fastest with tertiary halides.
B) It exhibits first-order kinetics.
C) A better leaving group should make a faster reaction.
D) All bonds are broken and formed in a single step.
11. What is the major elimination product obtained from the following reaction?
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15. Which of the following is the most reactive substrate in an E2 reaction?
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16. Which of the following is the least reactive substrate in an E2 reaction?
17. Which of the following statements about an E1 mechanism is not true?

A) The reaction is fastest with tertiary alkyl halides.
B) A better leaving group makes the reaction rate increase.
C) The reaction follows first-order kinetics.
D) Stronger bases favor the E1 reaction.
18. Which of the following statements about an E1 mechanism is true?

A) The identity of the leaving group affects the rate of reaction.
B) The reaction follows second-order kinetics.
C) The reaction is slowest with tertiary substrates.
D) Polar aprotic solvents favor the E1 mechanism.
19. Which of the following is the most reactive substrate in an E1 reaction?
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20. Which of the following is the major elimination product of the following reaction?
21. Which of the following alkyl halides would afford the indicated product upon reaction
with sodium methoxide?
22. Which of the following is the major E2 product formed from the following alkyl halide?
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23. Which of the labeled protons in the compound below is most readily abstracted under
E2 conditions?
A) Ha B) Hb C) Hc D) Hd
24. Which of the following alkyl halides will afford the product below as the major product
in an E2 reaction?
25. What is the product of the following reaction?
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A) Only I B) Only II C) Only III D) II and III
29. Which of the following is most likely to react as a base rather than a nucleophile?
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30. Which of the following is most likely to react as a nucleophile rather than a base?
31. Which of the following is the dihalide that can be used to prepare the alkyne below?
32. Which of the following is the dihalide that can be used to prepare the alkyne below?
A) I and II B) II and III C) I and III D) I, II and III
33. Select the elimination product(s) formed by treating the indicated alkyl halide with a
base.
A) Only I B) Only II C) Only III D) I, II and III
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34. What is (are) the product(s) of the following reaction?
A) I and II B) II and III C) I and III D) I, II and III
36. What is (are) the elimination product(s) of the following reaction?
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37. What is (are) the elimination product(s) of the following reaction?
A) Only I B) Only II C) Only III D) I and II
40. What is (are) the starting material(s) in the reaction below?
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41. Which alkyl halide(s) would give the following alkene as the only product in an
elimination reaction?
42. What is the most likely mechanism for the reaction below?
A) SN1 B) SN2 C) E1 D) E2
43. What is the most likely mechanism for the reaction below?
A) SN1 B) SN2 C) E1 D) E2
44. Consider the following E2 reaction. What rate equation would be observed for this
reaction?
A) Rate = k[CH3CH2CH2Br]
B) Rate = k[CH3CH2CH2Br][KOC(CH3)3]
C) Rate = k[CH3CH2CH2Br][KOC(CH3)3]2
D) Rate = k[CH3CH2CH2Br]2[KOC(CH3)3]
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45. Which of the following alkenes is the most stable?
Chapter 9: Alcohols, Ethers and Epoxides
1. Which of the following compounds is (are) primary alcohols?
A) Only I B) Only II C) Only I and II D) Only II and III
2. Which of the following compounds is (are) secondary alcohols?
A) Only I B) Only II C) Only II and III D) Only III and IV
3. Which of the following compounds are ethers?
A) Only I and II B) Only III and IV C) Only I, II and III D) I, II, III and IV
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4. Which of the following compounds are epoxides?
A) Only I and III B) Only III and IV C) Only I, III and IV D) I, II, III and IV
5. Which of the following compounds is (are) symmetrical ethers?
A) Only I B) Only IV C) Only III and IV D) Only I, III and IV
6. Which of the following explains why epoxides are much more reactive than ethers?
A) The C-O-C bond angle of an epoxide is 109°, making epoxides have angle strain.
B) The oxygen atom of an epoxide is sp2 hybridized.
C) The C-O-C bond angle of an epoxide is 120°, making epoxides have angle strain.
D) The C-O-C bond angle of an epoxide is 60°, making epoxides have angle strain.
7. What is the IUPAC of the following compound?
(CH3CH2)3COH
A) 2-Ethyl-2-pentanol C) 3-Ethyl-3-pentanol
B) 2-Ethyl-3-pentanol D) 2,2-Diethyl-1-butanol
A) 3,3,6-Trimethylcyclohexanol C) 1,4,4-Trimethyl-2-cyclohexanol
B) 2,5,5-Trimethylcyclohexanol D) 1,1,4-Trimethyl-2-cyclohexanol
A) 5-Hydroxy-3-methyl-1-pentene C) 3-Methyl-1-penten-5-ol
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B) 3-Methyl-5-penten-1-ol D) 3-Methyl-4-penten-1-ol
A) (S)-2,2-Dimethyl-3-pentanol C) (R)-4,4-Dimethyl-3-pentanol
B) (R)-2,2-Dimethyl-3-pentanol D) (S)-1-tert-Butyl-1-propanol
A) Ethoxyoctane
B) 5-Ethoxyoctane
C) 4-Ethoxyoctane
D) Ethyl octyl ether
12. What is the common name of the following compound?
A) Isobutyl isopropyl ether C) Di-sec-butyl ether

B) Diisobutyl ether D) Diisopropyl ether
A) Methyl sec-butyl ether C) sec-Butyl methyl ether

B) Isobutyl methyl ether D) Butyl methyl ether
A) Methyl vinyl ether C) Propenyl methyl ether

B) Allyl methyl ether D) Methylene propylene ether
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A) 1,2-Epoxy-4-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane
B) 3,4-Epoxy-1-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane
A) 1,2-Epoxy-2-methylcyclopentane C) 1,2-Epoxy-1-methylpentane
B) 1,2-Epoxy-1-methylcyclopentane D) 1,2-Epoxy-2-methylpentane
A) 1,1-Dimethyloxirane C) 2-Methylpropylene oxide

B) 2-Methylpropylane D) 2,2-Dimethyloxirane
20. Rank the following compounds in order of increasing boiling point, putting the
compound with the lowest boiling point first.
A) III < II < I < IV C) IV < I < II < III
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B) II < III < I < IV D) I < II < III < IV
21. Which of the following statements about a crown ether-cation complex is not true?
A) It is a host-guest complex.
B) The crown ether is the guest and the cation is the host.
C) The crown ether is the host and the cation is the guest.
D) The host-guest complex is soluble in nonpolar solvents.
22. Which of the following reactions will provide the best yield of ether by the Williamson
ether synthesis?
A) Sodium methoxide and tert-butyl bromide.
B) Sodium tert-butoxide and iodomethane.
C) Methanol and tert-butyl alcohol in the presence of KOH.
D) Iodomethane and tert-butyl bromide in the presence of KOH.
23. Which of the following reactions will provide the best yield of ether by the Williamson
ether synthesis?
A) Bromobenzene and sodium methoxide.
B) Phenol and sodium methoxide.
C) Bromobenzene and bromomethane.
D) Sodium phenoxide and bromomethane.
24. Which of the following ethers cannot be prepared by the Williamson ether synthesis?
A) Isopropyl methyl ether C) tert-Butyl phenyl ether
B) tert-Butyl methyl ether D) Methyl phenyl ether
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25. Which of the following would be a reasonable synthesis of 1-butanol?
26. Which of the following would be a reasonable synthesis of 2-butanol?
27. What is the best choice of reagent to accomplish the following transformation?
A) HCl B) SOCl2, pyridine C) Cl2 D) H3O+, H2O
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29. What is the major organic product(s) obtained in the following reaction?
A) I B) II C) III D) I and II
A) HCl B) H2SO4 C) NaOH D) TsCl, pyridine
31. Which of the following alcohols reacts the fastest with HCl to give the corresponding
alkyl halide?
32. What is the major organic product obtained from the following sequence of reactions?
A) 2-Methyl-1-butene C) 1-Chloro-2-methylbutane
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B) 3-Methyl-3-butene D) 1-Bromo-2-methylbutane
33. Determine the product(s) of the following reaction.
A) Only I B) Only II C) Only III D) Only II and III
A) Only I B) Only II C) Only III D) Only I and II
35. Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting
the least reactive first.
A) I < III < II B) I < II < III C) II < III < I D) III < II < I
36. Which of the following statements about carbocation rearrangement is not true?
A) A less stable carbocation can rearrange to a more stable carbocation by shift of a
hydrogen atom.
B) A less stable carbocation can rearrange to a more stable carbocation by shift of an
alkyl group.
C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation.
D) The migrating group in a 1,2-shift moves with one bonding electron.
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37. Which of the following alcohols is most likely to yield a carbocation that is susceptible
to rearrangements?
A) TsCl, pyridine B) POCl3, pyridine C) HCl, ZnCl2 D) NaOH
39. What is the major organic product obtained from the following reaction?
A) (±)-2-Chlorobutane C) (S)-2-Chlorobutane
B) (R)-2-Chlorobutane D) trans-2-Butene
A) (R)-2-Methylpentanenitrile C) (±)-2-Methylpentanenitrile
B) (S)-2-Methylpentanenitrile D) trans-2-Butene
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A) (S)-2-Methoxypentane C) (±)-2-Methoxypentane
B) (R)-2-Methoxypentane D) trans-2-Butene
43. What are the major products obtained upon treatment of ethyl methyl ether with excess
HBr?
A) Bromomethane and ethanol C) Bromoethane and bromomethane
B) Bromoethane and methanol D) Ethanol and methanol
44. What are the major products obtained upon treatment of tert-butyl methyl ether with
excess HI?
A) tert-Butyl alcohol and iodomethane C) tert-Butyl alcohol and methanol
B) tert-Butyl iodide and iodomethane D) tert-Butyl iodide and methanol
45. Which of the following statements about the reaction of ethers with strong acids is true?
A) HCl, HBr and HI can all be used.
B) The mechanism of ether cleavage is SN1 only.
C) The mechanism of ether cleavage is SN2 only.
D) The mechanism of ether cleavage is SN1 and SN2.
46. What are the major products obtained upon treatment of methyl phenyl ether with
excess HBr?
A) Phenol and bromomethane C) Bromobenzene and bromomethane
B) Phenol and methanol D) Bromobenzene and methanol
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47. Determine the product in the following reaction (ignoring possible stereoisomers).
48. Determine the product in the following reaction (ignoring possible stereoisomers).
Chapter 10: Alkenes
1. Which of the following alkenes are terminal alkenes?
A) I and II B) II and III C) I and IV D) I and III
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2. Which of the following alkenes are internal alkenes?
A) I and II B) II and III C) I and III D) II and IV
3. Which of the statements about the properties of the carbon-carbon double bond is not
true?
A) There is restricted rotation around the carbon-carbon double bond.
B) Whenever the two groups on each end of a carbon-carbon double bond are the
same, two diastereomers are possible.
C) Trans alkenes are generally more stable than cis alkenes.
D) The stability of the carbon-carbon double bond increases as the number of
substituent groups increases.
4. Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl.
A) 1 B) 2 C) 3 D) 0
5. Calculate the degree of unsaturation for a molecule with molecular formula C8H9N.
A) 2 B) 3 C) 4 D) 5
A) 6-Ethyl-1-heptene C) 2-Ethyl-1-octene
B) 2-Ethyl-1-heptene D) 6-Ethyl-6-heptene
A) 1-Methylcyclopentene C) 1-Methylene-1-methylcyclopentane
B) 2-Methyl-1-cyclopentene D) 1-Methylcyclohexene
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A) 1,2-Dimethylcyclohexene C) 1,6-Dimethylcyclohexene
B) 2,3-Dimethylcyclohexene D) 1,2-Dimethyl-3-cyclohexene
A) 5-Methyl-5-hexen-2-ol C) 6-Hydroxy-2-methylheptene
B) 6-Methyl-6-hepten-2-ol D) 6-Hydroxy-2-methyl-1-heptene
A) 4-Ethyl-3-methyl-1-octen-5-ol C) 5-Ethyl-6-methyl-7-octen-4-ol
B) 3-Ethyl-4-methyl-2-octen-5-ol D) 4-Ethyl-6-methyl-1-octen-5-ol
11. Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.
A) I = Z and II = Z C) I = E and II = E
B) I = Z and II = E D) I = E and II = Z
A) 2-Vinylcyclohexene C) 1-Allylcyclohexene
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B) 2-Allylcyclohexene D) 1-Vinylcyclohexene
13. Rank the following isomers in order of increasing boiling point, putting the least first.
A) I < II < III B) I < III < II C) II < III < I D) II < I < III
15. Which of the following is a terpene?
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17. Which of the following statements about alkenes is not true?

A) They are less reactive than alkanes.
B) They can exist as cis/trans isomers.
C) The bond angle around the C-C double bond is approximately 120°.
D) The carbon of the C-C double bond is sp2 hybridized.
18. Which of the following statements about alkenes is true?

A) Alkenes react with nucleophiles and bases.
B) Alkenes contain double bonds from two sp-hybridized carbon atoms.
C) In the reactions of alkenes, the  bond is not always broken.
D) Alkenes react with electrophiles.
19. Rank the following compounds in order of decreasing stability, putting the most stable
first.
A) I > II > III B) II > I > III C) III > II > I D) III > I > II
20. Which of the following reaction conditions would result in anti-Markovnikov addition
to an alkene?
A) H2O/H3O+ B) HBr C) HCl D) [1] BH3; [2] H2O2/HO-
21. Which of the following alkenes will undergo a carbocation rearrangement when reacting
with H2O in the presence of a small amount of H2SO4?
A) Only I and II B) Only I and III C) Only II and III D) I, II and III
22. In which of the following alkene addition reactions will carbocation rearrangements
occur?
A) Addition of Br2 and H2O
B) Addition of Br2
C) Addition of Cl2 and H2O
D) Addition of H2O in the presence of H2SO4
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23. Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?

A) Initial attack by bromide anion (Br-). C) Formation of a primary carbocation.
B) Initial attack by bromine radical (Br•). D) Formation of a secondary carbocation.
24. Rearrangements can occur in which of the following reactions?

A) Addition of Cl2 to an alkene. C) Addition of H2O/H3O+ to an alkene.
B) Addition of HOBr to an alkene. D) None of the above.
25. Which of the following alkenes reacts fastest with HCl?
26. Predict the major product of the following reaction.
27. Predict the product(s) of the following reaction.
A) Only I and II B) Only I and III C) Only II and III D) Only III and IV
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28. Predict the product of the following reaction.
31. Predict the major product(s) of the following reaction.
A) Only I and II B) Only II and III C) Only III and IV D) Only I and IV
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32. Predict the major product(s) of the following reaction.
A) Only I and II B) Only II and IV C) Only II and III D) Only I and IV
33. What is the major product obtained from the following reaction?
34. What is the major product obtained from the following reaction (assume enantiomer is
also formed)?
35. What is (are) the major product(s) obtained from the following reaction?
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36. What is (are) the major product(s) obtained from the following reaction?
A) HBr B) Br2, H2O C) Br2 D) H2O2/Br2
A) H2O, Br2
B) [1] BH3; [2] H2O2/HO-
C) H2O, H2SO4
D) [1] BH3; [2] H2O
39. What type of reactive intermediate is formed in the reaction of an alkene with HI to give
an iodoalkane?
A) Carbanion B) Carbocation C) Cyclic bromonium ion D) Radical
40. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and
H2O to give a bromohydrin?
A) Carbanion B) Radical C) Carbocation D) Cyclic bromonium ion
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41. Rank the carbocation in order of increasing stability, putting the least stable first.
A) III < I < II B) III < II < I C) I < II < III D) I < III < II
42. Which of the following statements about the stereochemistry of electrophilic addition of
HX to alkenes is true?
A) Achiral starting materials yield an unequal mixture of two enantiomers.
B) Hydrohalogenation occurs with syn stereochemistry only.
C) Hydrohalogenation occurs with anti stereochemistry only.
D) Hydrohalogenation occurs with syn and anti addition of HX.
43. Which of the following reactions of alkenes takes place with anti stereochemistry only?
A) Addition of HBr
B) Addition of H2O in the presence of H2SO4
C) Addition of BH3 followed by H2O2/HO-
D) Addition of Br2
44. Predict the product of the following reaction, ignoring stereochemistry.
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45. What is the starting material in the following reaction?
46. What is (are) the missing reagent(s) in the following reaction?
A) Br2/CCl4 C) [1] Br2; [2] H2O

B) NBS, DMSO/H2O D) [1] BH3; [2] H2O2/HO-
47. Which of the following statements about hydroboration/oxidation of alkenes is true?

A) In hydroboration, the boron atom bonds to the more substituted carbon.
B) Hydroboration occurs with anti addition.
C) Oxidation occurs with retention of configuration.
D) 9-BBN does not undergo hydroboration in the same manner as BH3.
Chapter 11: Alkynes
1. Which of the following molecular formulas is consistent with the formula for a
molecule containing one alkyne and no other degrees of unsaturation?
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2. Which of the following represents a terminal alkyne?
A) Only I and II B) Only II and III C) Only I and III D) Only II and IV
3. Which of the following represents an internal alkyne?
A) Only I and II B) Only I and III C) Only II and IV D) Only II and III
4. Which of the following alkynes is a symmetrical alkyne?
5. How many degrees of unsaturation are introduced by a triple bond?

A) 0 B) 1 C) 2 D) 3
6. How many  bonds and  bonds are present in a triple bond?

A) One  bond and one  bond. C) Two  bonds and one  bond.
B) One  bond and two  bonds. D) Two  bonds and two  bonds.
7. Which of the following statements about alkynes is not true?

A) Alkynes undergo many addition reactions.
B) Alkynes are more polarizable than alkenes.
C) Both  bonds of a C-C triple bond are weaker than a C-C  bond.
D) The electrons in the  bonds of alkynes are more tightly held than those of alkenes.
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8. Give the IUPAC name for the following compound.
A) 6,6-Dimethyl-3-octyne C) 3,3-Dimethy-5-octyne
B) 3,3-Dimethyl-3-octyne D) 6-Ethyl-6-methyl-3-heptyne
A) 4,4-Diethyl-1-octyne C) 4,4-Dipropyl-6-heptyne
B) 4,4-Dipropyl-1-heptyne D) 4,4-Diethyl-6-octyne
A) 4-Chloro-4-methyl-2-heptyne C) 3-Chloro-3-methyl-4-hexyne
B) 3-Chloro-3-methyl-4-heptyne D) 4-Chloro-4-methyl-2-hexyne
A) 3-sec-Butyl-1,4-octadiyne C) 3-Isopropyl-1,5-nonadiyne
B) 3-Isopropyl-1,5-octadiyne D) 3-sec-Butyl-1,4-nonadiyne
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A) trans-2-Acetylenecyclohexanol C) trans-2-Acetylene-1-cyclohexanol
B) trans-2-Ethynylcyclohexanol D) trans-2-Ethylenecyclohexanol
A) 2,5-Dimethyl-3-heptyne C) 2,5-Dimethyl-3-octyne
B) 3,6-Dimethy-4-heptyne D) 3,6-Dimethyl-4-octyne
A) 4-Methyl-4-penten-1-yne C) 5-Methyl-4-hexen-1-yne
B) 2-Methyl-2-hexen-5-yne D) 2-Methyl-2-penten-4-yne
15. Which of the following about the physical properties of alkynes is not true?
A) Alkynes have low melting and boiling points.
B) Melting and boiling points increase as the number of carbons increases.
C) Alkynes are soluble in organic solvents.
D) Alkynes are soluble in water.
16. Which of the following explains why 1-pentyne has a slightly higher boiling point than
1-pentene?
A) 1-Pentyne has more carbons than 1-pentene.
B) 1-Pentyne has more carbons per hydrogen than 1-pentene.
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C) 1-Pentyne is linear while 1-pentene is trigonal planar.

D) The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1-
pentene.
18. What is the product of the following sequence of reactions?
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20. Which method would work the best in accomplishing the following transformation?
A) [1] HBr; [2] 2eq. NaNH2

B) [1] Br2; [2] 2eq. NaNH2
C) [1] Br2, H2O; [2] NaNH2
D) [1]BH3, THF; [2] H2O2, NaOH; [3] NaNH2
21. Which of the following statements about the reactions of alkynes is not true?
A) Alkynes contain easily broken  bonds.
B) Alkynes undergo addition reactions.
C) When alkynes undergo two sequential addition reactions, four new  bonds are
formed.
D) When alkynes undergo two sequential addition reactions, two new  bonds and a 
bond are formed.
22. Which of the indicated hydrogen in the following compounds is the least acidic?
23. Which of the indicated hydrogen in the following compounds is the most acidic?
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24. Rank the following compounds in order of decreasing basicity, putting the most basic
first.
A) I > II > III B) III > II > I C) III > I > II D) II > III > I
25. Which of the following anions is the most basic?
26. Which of the following bases can deprotonate acetylene? You are given the pKa values
of the conjugate acids in parentheses.
A) Only I and II B) Only I and III C) Only II and III D) Only II and IV
27. Which of the following bases cannot deprotonate acetylene? You are given the pKa
values of the conjugate acids in parentheses.
A) Only I and II B) Only I and III C) Only II and III D) Only II and IV
A) Only I B) Only II C) Only III D) I, II, III
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29. What is the reagent required to accomplish the following transformation?
A) SOCl2 B) 2eq. HCl C) Cl2 D) Br2/CCl4
30. In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is:
A) The Csp-H1s bond of 1-butyne. C) The H atom in HBr.
B) The C-C triple bond of 1-butyne. D) The Br ion.
31. In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is:
A) The Csp-H1s bond of 1-butyne. C) The H atom in HBr.
B) The C-C triple bond of 1-butyne. D) The Br ion.
A) Only I B) Only II C) Only III D) I, II, III
33. Which of the following statements about tautomers is true?

A) Tautomers differ in the position of a single bond and a hydrogen atom.
B) Tautomers differ in the position of a double bond and a carbon atom.
C) Tautomers differ in the position of a double bond and a hydrogen atom.
D) Tautomers differ in the position of a single bond and a carbon atom.
34. What is the relationship between the keto and enol forms of acetone, CH3COCH3?
A) Same compounds C) Enantiomers
B) Diastereomers D) Constitutional isomers
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35. Which of the following compounds is a tautomer of 2-hexanone?
A) Only I and II B) Only I and III C) Only II and III D) I, II, III
36. Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?
37. Which of the following represents a keto-enol tautomeric pair?
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38. What is the major organic product of the following reaction?
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43. What is (are) the major organic product(s) of the following reaction?
A) Only I and II B) Only II and III C) Only I and III D) I, II, III
44. Determine the product of the following reaction.
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Chapter 12: Oxidation and Reduction
1. Which of the following statements about oxidation and reduction is not true?
A) The conversion of an alkyne to an alkene is reduction.
B) The conversion of an alkene to an alkane is reduction.
C) Oxidation results in a decrease in the number of C-H bonds.
D) Reduction results in an increase in the number of C-Z bonds.
2. What is the correct classification of the following reaction?
A) Reduction reaction C) Elimination reaction

B) Oxidation reaction D) Substitution reaction



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11. Rank the following compounds in order of increasing oxidation level (from lowest to
highest).
A) I < III < II < IV C) IV < I < III < II
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B) II < III < I < IV D) II < IV < III < I
12. What happens to the carbon atom in the transformation of chloromethane to

methyllithium?
CH3Cl + 2Li  CH3Li + LiCl

A) Oxidized C) Oxidized and Reduced
B) Reduced D) Neither oxidized nor reduced
13. Rank the following compounds in order of decreasing oxidation level, putting the
compound with the highest oxidation level first.
A) II > IV > I > III C) III > I > II > IV

B) I > III > IV > II D) III > I > IV > II
14. Which of the following classes of organic compounds cannot undergo reduction easily?
A) Alkanes B) Alkenes C) Alkynes D) Carboxylic acids
A) I and III B) II and III C) I, II, III D) I or II
16. Rank the following alkenes in order of decreasing heat of hydrogenation.
A) I > II > III B) III > I > II C) II > I > III D) III > II > I
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17. Which of the following explains why heats of hydrogenation cannot be used to
determine the relative stability of compounds A and B below?
A) Compound A is trisubstituted while compound B is monosubstituted.

B) Compound A has E configuration while compound B has no E/Z configuration.
C) Both compounds A and B have no E/Z configurations.
D) Hydrogenation of A and B give different alkanes.
18. Rank the following alkenes in order of increasing rate of hydrogenation.
A) I < III < IV < II C) I < II < III < IV

B) IV < III < II < I D) IV < II < III < I
19. A compound X of molecular formula C8H12 with no triple bonds reacts with one
equivalent of H2 to give a new compound having molecular formula C8H14. What can be
inferred about the structure of compound X?
A) Compound X has 3 rings.
B) Compound X has 3  bonds.
C) Compound X has 1 ring and 2  bonds.
D) Compound X has 2 rings and 1  bond.
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21. What reagent is required to accomplish the following transformation?
A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst
22. What reagent is required to accomplish the following transformation?
A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst
25. Which of the following statements about the reduction of epoxides with LiAlH4 is true?
A) The nucleophile is a hydride (H-).
B) In unsymmetrical epoxides, nucleophilic attack of H- occurs at the more substituted
carbon atom.
C) The reaction follows SN1 mechanism.
D) The nucleophile, H-, is a weak nucleophile.
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26. Which is (are) the product(s) of the following reaction?
27. Which of the following products do not form in the following reaction?
A) Only I B) Only II C) Only III and IV D) Only I and II
29. Determine the product of the following reaction, ignoring stereochemistry.
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A) LiAlH4 C) RCO3H, H2O/HO-

B) [1] OsO4; [2] NaHSO3, H2O D) PCC/CH2Cl2
A) [1] OsO4; [2] NaHSO3, H2O C) RCO3H/H2O/HO-

B) KMnO4, H2O/HO- D) PCC/CH2Cl2
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34. After ozonolysis and treatment of the unstable ozonide with CH3SCH3, compound A
was converted to the compound below. What is the structure of compound A?
35. What is the starting material in the following sequence of reactions?
36. Which of the following is (are) formed by ozonolysis of compound A?
A) Only I B) Only II C) Only I and II D) I, II, III
37. Which of the following is (are) formed by ozonolysis of compound A?
A) Only I B) Only II C) I and II D) I, II, III
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38. Which of the following is (are) formed by ozonolysis of the following alkyne?
A) Only I and II B) Only III and IV C) Only I and IV D) Only II and III
39. Which of the following is (are) formed by ozonolysis of the following alkyne?
A) Only I B) Only II C) I and II D) I, II, III
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Chapter 13: Mass Spectrometry and Infrared Spectroscopy
1. In electron impact mass spectrometry (EIMS), what is being detected?

A) The molecular mass of the compound
B) The molecular formula of the compound
C) The mass to charge ratio of any ionic species
D) The mass to charge ratio of any neutral species
2. What type of feature will be observed in the EI mass spectrum of chlorobenzene?

A) An absorption at 3100 cm–1
B) A signal at 113.
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C) A signal at 112 and a signal at 114 in a ratio of 3:1

D) A signal at 112 and a signal at 114 in a ratio of 1:1
3. You observe a compound that exhibits a mass spectrum with peak at 160 and a peak at
162, both of equal intensity. This compound contains:
A) Two chlorine atoms C) One bromine atom
B) One iodine atom D) Two bromine atoms
4. What type(s) of molecular motion is (are) observed using infrared spectroscopy?

A) Stretching and bending C) Spin flipping
B) Rotation and excitation D) Fragmentation
5. The functional group region of an infrared spectrum is:

A) Where the cations appear C) Less than 1500 cm–1
B) Greater than or equal to 1500 cm–1 D) Greater than or equal to 2500 cm–1
6. Stronger bonds will be found where in the infrared spectrum?

A) Higher molecular weight C) Lower wavenumbers
B) Lower molecular weight D) Higher wavenumbers
7. Compared to a C–H bond, a C–D bond will vibrate where in the infrared spectrum?
A) Higher molecular weight C) Lower wavenumbers
B) Lower molecular weight D) Higher wavenumbers
8. Why does an alkyne carbon–carbon triple bond vibrate at a higher wavenumber than an
alkene carbon–carbon double bond?
A) It is stronger. C) It has fewer hydrogens.
B) It is weaker. D) It makes a less stable cation.
9. Why is the infrared absorption for the stretching motion of internal alkynes rarely
observed?
A) They do not form cations.
B) They are too strong.
C) Stretching in internal alkynes does not involve a change in dipole moment.
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D) They do not have hydrogens.
10. Consider the three organic compounds drawn below. Which of the following statements
is (are) true about the IR spectra of I, II, and III?
A) I shows strong absorptions at 2950 cm–1 and 1700 cm–1.

B) II shows strong absorptions at 2950 cm–1 and 2250 cm–1.
C) III shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1.
D) Statements (I shows strong absorptions at 2950 cm–1 and 1700 cm–1) and (III
shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1) are true.
11. In an IR spectrum, which of the indicated C–H bonds exhibits a stretching absorption at
the largest wave number?
12. Which of the following statements is (are) accurate about the IR spectrum of
compounds I, II, and III below?
A) Compound I shows absorptions at 2950 and 1700 cm–1.

B) Compound II shows absorptions at 3200–3600 and 1650 cm–1.
C) Compound III shows absorptions at 3200–3600 and 2950 cm–1.
D) Both (Compound I shows absorptions at 2950 and 1700 cm–1) and (Compound II
shows absorptions at 3200–3600 and 1650 cm–1) are true.
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13. Which of the indicated C–H bonds absorbs at the lowest wave number in the IR
spectrum?
14. Which of the following statements is (are) true about the IR spectrum of the compound
drawn below?
A) It shows absorptions at 3000–3150 cm–1 and 1720 cm–1.

B) It shows absorptions at 3000–2850 cm–1 and 2150 cm–1.
C) It shows absorptions at 2250 cm–1 and 1650 cm–1.
D) It shows absorptions at 2250 cm–1 and 1720 cm–1.
E) Both statements B (It shows absorptions at 3000–2850 cm–1 and 2250 cm–1) and D
(It shows absorptions at 2250 cm–1 and 1720 cm–1) are true.
15. A compound X shows a molecular ion peak at m/z 72 in its mass spectrum, and a strong
peak at ~1715 cm–1 in its IR spectrum. Which structures are possible for compound X?
16. A compound X has a molecular ion peak in its mass spectrum at m/z 136. What
information does this tell us about X?
A) X has a molecular mass of 136.
B) The molecular formula for X is C8H8O2.
C) The empirical formula for X is C4H4O.
D) Both A (X has a molecular mass of 136) and B (The molecular formula for X is
C8H8O2) are true.
E) Statements (X has a molecular mass of 136), (The molecular formula for X is
C8H8O2), and (The empirical formula for X is C4H4O) are all true.
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17. You are given a bottle of an organic liquid and told it must be either cyclohexane or 1-
hexene. Which of the following statements is (are) true about these two compounds?
A) The two compounds can be differentiated by their mass spectra because they will
have molecular ion peaks at different m/z.
B) 1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not.
C) Both cyclohexane and 1-hexene will show C–H absorptions at about 2950 cm–1.
D) Statements B (1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will
not) and C (Both cyclohexane and 1-hexene will show C–H absorptions at about
2950 cm–1) are both true.
E) Statements A (The two compounds can be differentiated by their mass spectra
because they will have molecular ions at different masses), B (1-Hexene will show
an absorption at 1650 cm–1 but cyclohexane will not), and (Both cyclohexane and
1- hexene will show C–H absorptions at about 2950 cm–1) are all true.
18. Which of the following statements is (are) true about a compound that has a molecular
ion peak in its mass spectrum at mass 104, and shows prominent peaks in its IR
spectrum at 3200–2850 cm–1?
A) The compound has a molecular mass of 104.
B) The compound contains a C=O group and Csp3-H hybridized bonds.
C) The compound contains an OH group and Csp3-H hybridized bonds.
D) Both (The compound has a molecular mass of 104) and (The compound contains a
C=O group and Csp3-H hybridized bonds) are true statements.
E) Both (The compound has a molecular mass of 104) and (The compound contains
an OH group and Csp3-H hybridized bonds) are true statements.
19. An alkyne C–H bond absorbs at higher wave number than an alkene C–H bond. What
does this tell you about the strength of these two bonds?
A) The alkene C–H bond is stronger. C) The alkene C–C bond is stronger.
B) The alkyne C–H bond is stronger. D) The alkyne C–C bond is stronger.
20. Which of the following statements is (are) true about a compound that has a molecular
ion peak in its mass spectrum at mass 94, and shows prominent peaks in its IR spectrum
at 3600–3200 and 1600 cm–1?
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B) The compound contains a C=O group and Csp3-H hybridized bonds.

C) The compound contains an OH group and a benzene ring.
D) Both A (The compound has a molecular mass of 94) and B (The compound
contains a C=O group and Csp3-H hybridized bonds) are true statements.
E) Both A (The compound has a molecular mass of 94) and C (The compound
contains an OH group and a benzene ring) are true statements.
21. Which of the following statement(s) is (are) true about a compound that has a molecular
ion peak in its mass spectrum at mass 69, and shows a prominent peak in its IR
spectrum at 2250 cm–1?
B) The compound contains a C=O group.
C) The compound contains a cyano or alkyne group.
D) Both (The compound has a molecular mass of 70) and (The compound contains a
C=O group) are true statements.
E) Both (The compound has a molecular mass of 70) and (The compound contains a
cyano or alkyne group) are true statements.
22. Which of the following statements is (are) true about a compound that has molecular ion
peaks in its mass spectrum at mass 170 and 172, and shows prominent peaks in its IR
spectrum at 3150–3000 and 1600 cm–1?
A) The compound is not pure.
B) The compound contains a halogen.
C) The compound contains an OH group and Csp3-H hybridized bonds.
D) Both A (The compound is not pure) and B (The compound contains a halogen) are
true statements.
E) Both A (The compound is not pure) and C (The compound contains an OH group
and Csp3-H hybridized bonds) are true statements.
23. Which of the following structures is consistent with a compound that displays a
molecular ion peak at 103 and infrared signals at 2250 and 1600 cm–1?
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molecular ion peak at 56 and infrared signals at 2250 and 3600–3200 cm–1?
molecular ion peak at 84 and infrared signals at 3000–2850 cm–1 and no signals between
3000-3300 cm-1?
26. What type of signal(s) would you observe in the mass and (or) infrared spectrum of the
following compound?
A) A signal at 1600 cm–1 C) A single mass peak at 92 amu

B) A signal at 3300 cm–1 D) Two mass peaks at 92 and 94 amu
27. What type of signal(s) would you observe in the mass and/or infrared spectrum of the
following compound?
A) A signal at 96 amu C) A signal at 1600 cm–1

B) Two signals at 112 and 114 amu D) A signal at 1720 cm–1
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28. What type of signal(s) would you observe in the mass and (or) infrared spectrum of the
following compound?
A) A signal at 95 amu C) Two signals at 95 and 94 amu

B) A signal at 94 amu D) A signal at 3600–3200 cm–1
29. In a typical mass spectrum, a smaller signal is observed at a mass 1 amu higher than the
molecular ion peak. Why?
A) Due to small impurities in the sample
B) Machine error
C) Because a small percentage of the compound will have a carbon that is the isotope
13
C instead of 12C
D) Because of fragmentation
30. Examine the IR below and classify the compound.
A) Alkane B) Carboxylic acid C) Alcohol D) Alkene
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A) Alcohol B) Aldehyde C) Amine D) Ketone E) Carboxylic acid
A) Alcohol B) Arene C) Amine D) Ketone E) Carbocylic acid
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A) Alcohol B) Aldehyde C) Carboxylic acid D) Ketone
A) Alcohol B) Aldehyde C) Amine D) Ketone
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13
35. C NMR is a technique in which the total number of signals represents the number of
unique carbon atoms in a molecule. Propose a structure that is consistent with the
following data.
a) The IR includes peaks at 1603 and 1495 cm-1.
b) The 13C NMR has a total of 7 signals.
c) The compound has one acidic proton.
36. The base peak in a mass spectrum corresponds to the most stable fragment. Propose a
structure for a compound that is consistent with the following data.
a) The molecular ion peak has m/z = 116
b) The base peak is at m/z = 59.
c) The compound is composed of C, H and O atoms.
d) The IR spectrum shows a strong absorbance at 3257 cm-1.
37. An IR spectrum has the following potentially important absorptions: 3091, 3067, 2963,
2921, 2252, 1603, 1499, 1455, 1416, 1078, 1031, 941, 735, and 696 cm-1. Indicate
which structure corresponds to the IR data.
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38. When the phenol shown below is treated with KOH, it forms a product whose IR
spectrum does not show an absorption in the 3200-3600 cm-1 region. Propose a
structure for the product.
39. Which of the following information is primarily obtained from an IR spectrum?

A) Conjugated  system present in a compound.
B) Functional groups present in a compound.
C) Molecular weight of a compound.
D) The carbon and hydrogen framework of a compound.
40. Which of the following compounds will have the lowest wavenumber for carbonyl
absorption?
41. Which of the following  bonds is IR inactive?
42. Which of the following statements about the base peak of a mass spectrum is always
true?
A) The base peak corresponds to the molecular ion.
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B) The base peak corresponds to the most abundant ion.

C) The base peak corresponds to the lowest m/z.
D) None of the above.
Chapter 14: Nuclear Magnetic Resonance Spectroscopy
1. How many unique protons are present in each of the following compounds?
A) I = 6; II = 3; III = 6. C) I = 6; II = 4; III = 4.
B) I = 5; II = 4; III = 6. D) I = 6; II = 4; III = 6.
2. How many peaks would be observed for each of the circled protons in the compounds
below?
A) I = 2; II = 6; III = 1. C) I = 1; II = 5; III = 1.
B) I = 3; II = 5; III = 2. D) I = 2; II = 6; III = 2.
3. Into how many peaks will each of the circled protons be split?
A) I = 3; II = 8; III = 1; IV = 4; V = 3. C) I = 4; II = 8; III = 2; IV = 4; V = 5.
B) I = 9; II = 8; III = 2; IV = 4; V = 4. D) I = 4; Ii = 7; III = 2; IV = 4; V = 3.
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below?
A) I = 8; II = 4; III = 3; IV = 3. C) I = 7; II = 3; III = 3; IV = 3.
B) I = 7; II = 4; III = 3; IV = 4. D) I = 7; II = 4; III = 2; IV = 4.
5. How many different kinds of protons are present in each of the following molecules?
A) I = 3; II = 5; III = 5; IV = 4; V = 3. C) I = 4; II = 5; III = 5; IV = 4; V = 3.
B) I = 4; II = 5; III = 4; IV = 4; V = 3. D) I = 4; II = 5; III = 5; IV = 3; V = 4.
6. Into how many peaks will each of the circled protons be split?
A) I = 3; II = 7; III = 4. C) I = 2; II = 7; III = 3.
B) I = 2; II = 7; III = 4. D) I = 2; II = 6; III = 4.
below?
A) I = 6; II = 2; III = 3. C) I = 7; II = 1; III = 3.
B) I = 7; II = 3; III = 3. D) I = 7; II = 2; III = 3.
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below?
A) I = 1; II = 4; III = 7. C) I = 2; II = 4; III = 7.
B) I = 3; II = 3; III = 7. D) I = 2; II = 4; III = 6.
9. How many different kinds of protons are present in each of the following compounds?
A) I = 4; II = 3; III = 1. C) I = 4; II = 4; III = 2.
B) I = 4; II = 4; III = 1. D) I = 3; II = 3; III = 1.
A) I = 2; II = 4; III = 6. C) I = 3; II = 3; III = 5.
B) I = 2; II = 4; III = 4. D) I = 2; II = 4; III = 5.
A) I = 6; II = 5; III = 3. C) I = 7; II = 6; III = 3.
B) I = 7; II = 5; III = 3. D) I = 6; II = 6; III = 3.
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12. How many different kinds of protons are present in each of the following molecules?
A) I = 6; II = 3; III = 4. C) I = 6; II = 4; III = 5.
B) I = 5; II = 3; III = 4. D) I = 6; II = 4; III = 4.
A) I = 2; II = 3; III = 4. C) I = 3; II = 3; III = 3.
B) I = 2; II = 3; III = 3. D) I = 3; II = 3; III = 4.
A) I = 4; II = 4; III = 4. C) I = 3; II = 3; III = 5.
B) I = 4; II = 4; III = 5. D) I = 3; II = 4; III = 5.
15. Which of the labeled protons absorbs furthest upfield in the 1H NMR spectrum?
16. Which of the following compounds does not show only one signal in its 1H NMR
spectrum?
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17. Which of the indicated protons in the molecules below would absorb furthest downfield
in a 1H NMR spectrum?
18. Which of the labeled protons would absorb furthest downfield in a 1H NMR spectrum?
19. Which of the indicated protons would absorb furthest downfield in a 1H NMR
spectrum?
20. Which compound does not give four sets of absorptions in its 1H NMR spectrum (i.e.,
which compound does not have four unique hydrogens)?
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21. Compound X has a molecular formula C8H10, and gives the 1H NMR spectrum below.
What is the structure of X?
A) A B) B C) C D) D
A) a: 5; b: 6 B) a: 5; b: 5 C) a: 4; b: 6 D) a: 4; b: 5
23. Into how many peaks will the circled proton be split?
A) 5 B) 6 C) 7 D) 8
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24. Which of the indicated protons absorbs furthest downfield?
25. For each of the following compounds, indicate how many 13C NMR signals will be
observed.
A) a: 4; b: 4; c: 7; d: 4 C) a: 4; b: 7; c: 7; d: 3
B) a: 5; b: 4; c: 7; d: 3 D) a: 5; b: 4; c: 6; d: 5
26. For each of the following compounds, indicate how many 13C NMR signals will be seen.
A) a: 3; b: 3; c: 5; d: 3 C) a: 3; b: 4; c: 5; d: 3
B) a: 4; b: 3; c: 5; d: 3 D) a: 4; b: 3; c: 3; d: 3
27. Which of the following compounds would give rise to a 13C spectrum with 6 peaks?
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28. An unknown compound X has the empirical formula C3H6O and a molecular ion in its
mass spectrum at 116. Compound X shows no IR absorption at 3200-3600 cm-1 but
shows a peak at 1700 cm-1. The 1H NMR spectral data of X is shown below. What is the
structure of compound X?
29. What is the relationship between Ha and Hb in the following compound?
A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic
30. What is the relationship between Ha and Hb in the following compound?
A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic
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31. An unknown compound X has the molecular formula C6H14O. Compound X shows a
strong peak in its IR spectrum at 3000 cm-1. The 1H NMR spectral data of compound X
is given below. What is the structure of compound X?
32. An unknown compound X has the molecular formula C7H13OBr. Compound X shows a
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33. An unknown compound X has the molecular formula C6H12O2. Compound X shows a
34. An unknown compound X has the molecular formula C6H14O. Compound X shows a
peak in its IR spectrum at 3200-3600 cm-1. The 1H NMR spectral data for compound X
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35. An unknown compound X has the molecular formula C10H11O2Br. Compound X shows a
strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for
compound X is given below. What is the structure of compound X?
A) Only I B) Only II C) Only III D) I or II
36. How could spectroscopy be used to distinguish between the following compounds?
A) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm.

B) Compound B has a peak at 3200-3500 cm-1 in its IR spectrum.
C) Compound A has a peak in its IR spectrum at 2900 cm-1.
D) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm and compound B has
a peak at 3200-3500 cm-1 in its IR spectrum.
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37. An unknown compound A has the molecular formula C7H14O2. Compound A absorbs
strongly in the IR at 1700 cm-1. The 1H NMR spectral data for compound A are given
below. What is the structure of compound A?
38. An unknown compound A has the molecular formula C12H16O. Compound A absorbs
strongly in the IR at 1700 cm-1. The NMR spectral data for compound A are given
below. What is the structure of compound A?
39. Which of the following statements about 13C NMR is not true?
A) In 13C proton-decoupled NMR spectra, all peaks are singlets.
13
B) C NMR spectra display peaks for only carbons that bear hydrogen atoms.
13
C) C NMR chemical shifts occur over a greater range than 1H NMR chemical shifts.
13
D) C NMR easily differentiates between the different hybridized carbons (sp3, sp2
and sp hybridized carbons).
40. What region of the electromagnetic spectrum does nuclear magnet resonance
spectroscopy use?
A) Radio frequency D) Visible frequency
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B) Microwave frequency E) Ultraviolet frequency

C) Infrared frequency
41. An unknown compound has the formula of C9H12. The following 1H NMR peaks were
observed:
Doublet at  1.22
Septet at  2.83
Multiplet at  7.09
From the data above, pick the compound below that fits the spectra data.
42. Which of the following statements is true about electromagnetic radiation?

A) All molecules absorb electromagnetic radiation at some frequency.
B) Frequency is directly proportional to wavelength.
C) NMR uses the microwave region of the electromagnetic spectrum.
D) The radio frequency region of the electromagnetic spectrum has the largest energy
per photon.
E) Energy is inversely proportional to frequency.
43. Which of the following spectroscopy methods does not involve the interaction of
organic molecules with electromagnetic radiation?
A) Nuclear Magnetic Resonance C) Mass spectroscopy
B) Infrared spectroscopy D) Ultraviolet spectroscopy
Chapter 15: Radical Reactions
1. Which of the following statements about radicals and radical reactions is not true?
A) Most radicals are unstable.
B) A radical contains an atom that has an octet of electrons.
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C) Half-headed arrows are used to show the movement of lone electrons.

D) A radical is formed by homolysis of a covalent bond.
2. Which of the following statements about carbon radicals is not true?

A) Carbon radicals are classified as primary, secondary, tertiary, or quaternary.
B) A carbon radical is sp2 hybridized.
C) The geometry of a carbon radical is trigonal planar.
D) The unhybridized p orbital in a carbon radical contains the unpaired electron.
3. Which of the following statements about radicals is true?

A) Cleavage of a stronger bond forms the more stable radical.
B) The stability of a radical increases as the number of alkyl groups bonded to the
radical carbon decreases.
C) The higher the bond dissociation energy for a C-H bond, the more stable the
resulting carbon radical.
D) Less stable radicals generally do not rearrange to more stable radicals.
4. Which of the following compounds contain primary (1°) radical carbons?
A) Only I B) Only II C) Only III D) Only II and IV
5. Which of the following compounds contain secondary (2°) radical carbons?
6. Which of the following compounds contain tertiary (3°) radical carbons?
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7. Which of the following is a radical scavenger?

A) O3 B) O2 C) Vitamin C D) CO2
8. How many monochlorination products can be formed (constitutional isomers only) from
the reaction of (CH3)2CHCH2CH3 with Cl2 and h?
A) 2 B) 3 C) 4 D) 5
9. How many monochlorination products can be formed (constitutional isomers only) from
the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and h?
A) 3 B) 4 C) 5 D) 6
10. How many monochlorination products can be formed from the reaction of (CH3)3CH
with Cl2 and h?
A) 1 B) 2 C) 3 D) 4
11. Which of the following statements about radical reactions is not true?
A) Light or heat provides the energy needed for homolytic bond cleavage to form
radicals.
B) Breaking the weak O-O bond of peroxides initiates radical reactions.
C) The diradical O2 removes radicals from a reaction mixture.
D) Radicals rearrange.
12. Which step is the rate-determining step in the mechanism of radical halogenation?
A) Initiation
B) Propagation
C) Termination
D) Initiation and Propagation
13. Which of the following statements about the propagation steps in the chlorination of
ethane is true?
A) Radical chlorination consists of two propagation steps.
B) The energy diagram for the propagation steps has three energy barriers.
C) The first of the propagation steps is rate-determining because its transition state is
at lower energy.
D) The second of the propagation steps is rate-determining because its transition state
is at higher energy.
14. Which of the following statements about chlorination and bromination is true?
A) Bromination is unselective, yielding a mixture of products.
B) Chlorination is often selective, yielding one major product.
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C) Chlorination is faster than bromination.

D) Bromination is faster than chlorination.
15. Which of the following statements about bromination is true?

A) The rate-determining step in bromination is exothermic.
B) Both radicals are formed.
C) A mixture of products results.
D) A single radical halogenation product predominates.
16. Which of the following statements about chlorination is true?

A) The rate-determining step in chlorination is endothermic.
B) The transition state resembles the product.
C) The more stable radical is formed faster.
D) A mixture of products results.
17. What is the product in the following sequence of reactions?
18. What is the product in the following sequence of reactions?
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19. Which of the following statements about the stereochemistry of halogenation reactions
is true?
A) An achiral starting material always gives an achiral product only.
B) An achiral starting material always gives a racemic product only.
C) The configuration at a stereogenic center of a product must change even if a
reaction does not occur at a stereogenic center.
D) An achiral starting material always gives either an achiral or a racemic product.
20. How many monochlorination products (constitutional isomers and stereoisomers) are
formed from the reaction of butane with Cl2 and h?
A) 2 B) 3 C) 4 D) 5
21. How many monochlorination products (constitutional isomers and stereoisomers) are
formed from the reaction of pentane with Cl2 and h?
A) 2 B) 3 C) 4 D) 5
22. Rank the following radicals in order of increasing stability, putting the least stable first.
A) III IV > III > I C) IV > III > II > I

B) III > II > IV > I D) IV > III > I > II
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26. How many allylic halides can be formed when 3-methycyclohexene undergoes allylic
halogenation with one equivalent of NBS and light?
A) 1 B) 2 C) 3 D) 4
28. Identify the monomer used to make the following polymer.
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31. Determine the monochlorination product(s)
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34. Which of the following statements is (are) true about free radical halogenation of
alkanes?
A) The first of the chain-propagating steps is rate-determining.
B) The reaction proceeds by way of a flat sp2 hybridized free radical.
C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a
carbon radical and a hydrogen atom.
D) Statements (The first of the chain-propagating steps is rate-determining) and (The
reaction proceeds by way of a flat sp2 hybridized free radical) are both true.
35. Which of the labeled hydrogens is most easily abstracted in a free radical bromination
reaction?
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36. Which of the indicated hydrogens is most readily abstracted in a free radical
halogenation reaction?
37. A possible reaction of ethane with chlorine is shown below.
This reaction could conceivably occur by the following chain mechanisms [1], [2], and
[3]. The chain initiating step(s) is (are) _____.
A) Only [1] B) Only [2] C) Only [3] D) Only [1] and [2]
[3]. The chain propagating step(s) is (are) _______.
A) Only [1] and [2] B) Only [2] and [3] C) Only [1] and [3] D) Only [3]
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[3]. Determine H for step [1].
Bond dissociation energies (kcal/mol):
A) -5 kcal/mol C) -28 kcal/mol

B) +58 kcal/mol D) None of the choices are correct.
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[3]. Determine H for step [2].
Bond dissociation energies (kcal/mol):
A) -5 kcal/mol C) -28 kcal/mol

B) +58 kcal/mol D) None of the choices are correct.
41. Select the route that would most likely produce the desired results from the given
starting material.
I. (1) H2SO4 and heat; (2) HBr

II. (1) KOH in ethanol; (2) HBr
III. (1) H2SO4 and heat; (2) HBr + peroxides
IV. (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides
42. What type of reactive intermediate is formed in the reaction of propene with N-
bromosuccinimide (NBS) to give 3-bromo-1-propene?
A) Cyclic bromonium ion C) Allylic carbanion
B) Allylic carbocation D) Allylic radical
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43. Which of the following alkenes undergoes allylic bromination to form a single
monobrominated product?
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Chapter 16: Conjugation, Resonance, and Dienes
1. Which of the following dienes contain conjugated double bonds?
2. Which of the following dienes contain isolated double bonds?
3. Which of the following statements about resonance structures is true?

A) The placement of atoms is different.
B) The placement of  bonds is different.
C) The placement of  bonds is different.
D) The placement of nonbonded electrons is the same.
4. What is the hybridization around the indicated carbon atom in the following anion?
5. What is the hybridization around the indicated oxygen atom in the following anion?
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6. Which of the following is (are) conjugated dienes?
7. Which of the following compounds is conjugated?
8. Which of the following conjugated dienes represent two conformations?
A) Only I and II
B) Only I and III
C) Only II and III
D) None of the choices
9. Rank the following dienes in order of decreasing heat of hydrogenation, putting the
diene with the highest heat of hydrogenation first.
A) I > II > III B) III > II > I C) II > I > III D) III > I > II
10. Rank the following compounds in order of increasing stability, putting the least stable
first.
A) I < II < III B) III < II < I C) II < I < III D) III < I < II
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11. What is the reactive intermediate in the reaction of 1,3-diene with HBr, resulting in 1,4-
addition?
A) Allylic radical C) Dienophile
B) Cyclic bromonium ion D) Allylic carbocation
12. Which of the following is the appropriate term for the mechanism of the addition of HBr
to 1,3-dienes?
A) Nucleophilic addition C) Free radical addition
B) Electrophilic addition D) Conjugate addition
13. What is (are) the major product(s) of the following reaction?
A) Only I B) Only II and IV C) Only I and III D) Only I, II and III
A) Only I B) Only I and III C) Only II and IV D) Only I, II, and III
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A) Only I B) Only II C) Only I and II D) I, II, III
16. Which of the following is not a product obtained from the addition of 1 equivalent of
HBr to (E)-1,3-pentadiene?
A) (E)-4-Bromo-2-pentene C) 3-Bromo-1-pentene
B) (E)-1-Bromo-2-pentene D) (E)-3-Bromo-2-pentene
17. What is the thermodynamic product obtained from the addition of 1 equivalent of HBr
to 1,3-butadiene?
A) 3-Bromo-1-butene C) 2-Bromo-2-butene
B) 1-Bromo-2-butene D) 2-Bromo-1-butene
18. What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3-
butadiene?
A) 3-Bromo-1-butene C) 2-Bromo-2-butene
B) 1-Bromo-2-butene D) 2-Bromo-1-butene
19. Which of the following statements about kinetic vs. thermodynamic products is true?
A) The product that is formed faster is the thermodynamic product.
B) The kinetic product predominates at low temperature.
C) The product that predominates at equilibrium is the kinetic product.
D) The thermodynamic product is less stable.
20. Which of the following statements about the mechanism of the Diels-Alder reaction is
true?
A) Three pi bonds break; two sigma bonds and one pi bond form.
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B) Three pi bonds break; one sigma bond and two pi bonds form.
C) Two pi bonds break; one sigma bond and one pi bond form.
D) Two pi bonds break; two sigma bonds and one pi bond form.
21. Which of the following is not a feature of the Diels-Alder reaction?

A) They are initiated by peroxides. C) Three pi bonds break.
B) They form new six-membered rings. D) They are concerted.
22. Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction,
listing the least reactive first.
A) I < II < III B) III < I < II C) II < I < III D) I < III < II
23. Which of the following is the least reactive diene in a Diels-Alder reaction?
24. Which of the following statements about the Diels-Alder reaction is true?
A) The diene can react only when it adopts the s-trans conformation.
B) Electron-withdrawing substituents in the diene increase reaction rate.
C) Electron-donating substituents in the dienophile increase the reaction rate.
D) The stereochemistry of the dienophile is retained in the product.
25. Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction,
listing the least reactive first.
A) I < II < III B) III < I < II C) II < I < III D) III < II < I
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26. Which of the following compounds is the least reactive dienophile in a Diels-Alder
reaction?
27. Which of the following compounds is the most reactive dienophile in a Diels-Alder
reaction?
28. Which of the following is the most reactive diene in a Diels-Alder reaction?
29. Which of the following is the least reactive diene in a Diels-Alder reaction?
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A) Only I B) Only I and II C) Only II and III D) I, II, III
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36. What diene and dienophile are used in a Diels-Alder reaction to prepare the following
compound?
37. Which of the following compound absorbs UV light at the longest wavelength?
38. Which of the following compound absorbs UV light at the longest wavelength?
39. Which of the following electronic transitions is common in the UV spectrum of 1,3-
butadiene?
A)    B)   * C) n  * D)   *
40. What is the definition of a resonance structure?

A) Compounds with the same molecular formula
B) Compounds with different carbon frameworks
C) Structures that differ only in the placement of pi and nonbonding electrons
D) Structures that differ only in the location of bonds
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41. Rank the following anions from most to least stable, listing the most stable first.
A) I > II > III B) III > II > I C) I > III > II D) III > I > II
42. How would you favor the formation of the kinetic product of the following reaction?
A) Excess HBr
B) Long reaction time
C) Low temperature
D) High pressure
43. Which of the following is an example of a bridged bicyclic system?
44. Why would the compound below not react with a dienophile in a Diels-Alder reaction?
A) The compound is not a conjugated diene.

B) There are no electron withdrawing groups on the compound.
C) There are no electron donating groups on the compound.
D) The compound can not adopt the s-cis conformation.
Chapter: Chapter 17: Benzene and Aromatic Compounds
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Multiple Choice
1. Which of the following statements about benzene is true?

A) Benzene is a saturated hydrocarbon.
B) Benzene undergoes addition reactions.
C) Benzene has five degrees of unsaturation.
D) Benzene undergoes substitution reactions.
2. Which of the following statements about the structure of benzene is not true?
A) Benzene is planar.
B) Benzene has three short double bonds alternating with three longer single bonds.
C) The electrons in the pi bonds are delocalized around the ring.
D) Benzene has six pi electrons.
3. What orbitals are used to form the bond indicated in the following molecule?
A) Csp2  Csp2
B) Csp2  C2p
C) C2p  C2p
D) Csp3  Csp3
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A) 3,6-Dichloroaniline
B) 2,5-Dichloroaniline
C) 2,5-Dichloroaminobenzene
D) 2,5-Dichloroanisole
A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid
A) 1-Chloro-4-ethyl-3-propylbenzene
B) 1-Chloro-4-ethyl-5-propylbenzene
C) 4-Chloro-1-ethyl-2-propylbenzene
D) 4-Chloro-2-propyltoluene
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A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole
8. What is the correct assignment of the names of the following substituted benzenes?
A) I = Phenol; II = anisole; III = toluene.

B) I = Benzaldehyde; II = phenol; III = anisole.
C) I = Benzaldehyde; II = phenol; III = toluene.
D) I = Phenol; II = anisole; III = styrene.
9. What is the correct assignment of the names of the following substituted benzenes?
A) I = Styrene; II = aniline; III = anisole.

B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.
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10. How many 13CNMR signals does the following compound exhibit?
A) 4
B) 5
C) 6
D) 8
11. What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR
absorption at 3150  2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H);
4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm.
A) I
B) II
C) III
D) IV
12. What is the correct assignment of the number of signals in the 13C NMR spectra of the
following disubstituted benzene derivatives?
A) I = 3 signals; II = 3 signals; III = 2 signals.

B) I = 3 signals; II = 4 signals; III = 2 signals.
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C) I = 6 signals; II = 6 signals; III = 6 signals.

D) I = 3 signals; II = 4 signals; III = 3 signals.
13. Which of the following is not one of the Hückel's criteria for aromaticity?
A) The molecule must be cyclic.
B) The molecule must be planar.
C) The molecule must be completely conjugated.
D) The molecule must have 4n pi electrons.
14. Which of the following is not a criterion for antiaromaticity?

A) The molecule must be cyclic.
B) The molecule must have (4n + 2) pi electrons.
C) The molecule must be planar.
D) The molecule must be completely conjugated.
15. What is the correct assignment of the names of the following aromatic heterocycles?
A) I = pyridine; II = pyrimidine; III = furan.

B) I = pyrimidine; II =pyrrole; III = furan.
C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
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16. What is the correct assignment of the names of the following fused aromatic compounds?
A) I = naphthalene; II = anthracene; III = phenanthrene.

B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.
17. Which of the following heterocycles is not aromatic?
A) I
B) II
C) III
D) IV
18. Which of the following ions is aromatic?
A) I
B) II
C) III
D) IV
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19. Which of the following molecules has the most acidic hydrogen atoms?
A) I
B) II
C) III
D) IV
20. Rank the following compounds in order of decreasing acidity, starting with the most acidic.
A) I > II > III

B) III > II > I
C) III > I > II
D) I > III > II
21. Which of the following ions is aromatic?
A) Only I and II
B) Only II and III
C) Only III and IV
D) Only II and IV
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22. Which of the following statements about the molecular orbital (MO) theory is true?
A) When two p orbitals of similar phase overlap side-by-side, a * antibonding molecular
orbital is formed.
B) When two p orbitals of opposite phase overlap side-by-side, a  bonding molecular orbital is
formed.
C) A  bonding molecular orbital is higher in energy than the two atomic p orbitals from which
it is formed.
D) A * antibonding molecular orbital is higher in energy than the two atomic p orbitals from
which it is formed.
23. What orbitals are used to form the indicated bond?
A) sp3
B) sp2
C) p
D) sp3 and sp2
24. What orbitals are used to form the indicated bond?
A) sp3
B) sp2
C) p
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D) sp3 and sp2
25. What is the name of the following compound?
A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene
26. What is the name of the following compound?
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
27. What is the correct structure for aniline?
A) I
B) II
C) III
D) IV
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28. What is the correct structure for anisole?
A) I
B) II
C) III
D) IV
29. What is the correct structure for toluene?
A) I
B) II
C) III
D) IV
30. What is the correct structure for 1-bromo-2,4-dimethoxybenzene?
A) I
B) II
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C) III
D) IV
31. Where do the protons in benzene appear in the 1H NMR spectrum?

A) Around 1600 cm-1
B) Around 120 ppm
C) Around 0 ppm
D) Around 7 ppm
32. How many different proton signals would the following compound show in its 1H NMR
spectrum?
A) 1
B) 3
C) 5
D) 6
33. What compound is consistent with the following 1H NMR spectrum?
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A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene
34. What is the correct structure for para-bromotoluene?
A) I
B) II
C) III
D) IV
35. Which of the following compounds is not aromatic?
A) I
B) II
C) III
D) IV
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36. Which of the following compounds is not aromatic?
A) I
B) II
C) III
D) IV
37. Which of the following compounds is aromatic?
A) I
B) II
C) III
D) IV
38. Which of the following compounds is aromatic?
A) I
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B) II
C) III
D) IV
39. Why is the following compound not aromatic?
A) It has 4n pi electrons.
B) It is not cyclic.
C) It has 4n+2 pi electrons.
D) The  electron system is not continuous.
40. Why is the following compound not aromatic?
A) It has 4n electrons.
B) It is not cyclic.
C) It has 4n+2 electrons.
D) The  electron system is not continuous.
Chapter 18: Electrophilic Aromatic Substitution
1. What is the first step in the general mechanism for electrophilic aromatic substitution?
A) Protonation of the aromatic ring
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B) Deprotonation of the aromatic ring

C) Addition of the electrophile to the aromatic ring
D) Loss of the electrophile from the aromatic ring
2. What is the driving force for losing a proton as the last step in electrophilic aromatic
substitution?
A) To neutralize the base that is present C) To make the ring more reactive
B) To make room for the electrophile D) To rearomatize the ring system
3. What is the electrophile in aromatic nitration?

A) NO+ B) NO2+ C) NO3+ D) NO2H
4. What is the electrophile in aromatic sulfonation?

A) H2SO3 B) H2SO4 C) SO3+ D) HSO3+
5. Why is sulfuric acid used in aromatic nitration?

A) To keep the reaction from getting too basic
B) To form the active electrophile NO2+
C) To protonate the aromatic ring
D) To keep the reaction from getting too acidic
6. What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?

A) the tert-butyl cation
B) a complex of tert-butylchloride and aluminum chloride
C) a proton
D) aluminum chloride
7. Which of the following halides will not work as an electrophile in a Friedel-Crafts

alkylation reaction?
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8. What are the two effects that have to be considered to determine the influence a
substituent will have on electrophilic aromatic substitution?
A) Steric and electronic C) Inductive and resonance
B) Inductive and steric D) Resonance and electronic
9. Why is the nitro group a meta director?

A) Because it is sterically very large.
B) Because it adds electron density to the meta position, thus activating it.
C) Because it stabilizes the intermediate cation.
D) Because it removes more electron density from the ortho and para positions than
the meta position, thus deactivating the meta position less.
10. What is a major problem with Friedel-Crafts alkylation?

A) It requires high temperatures.
B) The conditions are too acidic.
C) The starting material is frequently over-alkylated.
D) The products coordinate with the aluminum chloride.
11. Which of the following statements about the mechanism of electrophilic aromatic
substitution is not true?
A) All electrophilic aromatic substitution reactions occur via a two-step mechanism.
B) The transition state of the first step is lower in energy.
C) The first step is the rate-determining step.
D) The second step is the fast step.
12. What will be the site that leads to the major mono substitution product for an
electrophilic aromatic substitution reaction of the following compound?
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21. Which of the following substituents are activators in electrophilic aromatic substitution?
A) CH3O  B) Cl  C) NO2  D) HSO3 
22. Which of the following substituents are deactivators in electrophilic aromatic

substitution?
A) HO  B) CH3NH  C) CH3O  D) (CH3)3N+ 
23. Which of the following substituents is an ortho, para director?

A)  CHO B)  COOH C)  NHCOR D)  CN
24. Which of the following substituents is a meta director?

A)  N(CH3)2 B)  OCH3 C)  NHCOCH3 D)  SO3H
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A) Only I B) Only II C) Only III D) Only I and III
27. Rank the following compounds in order of increasing reactivity in electrophilic aromatic
substitution.
A) I < II < III < IV C) III < IV IV > I > III C) IV > II > I > III

B) II > III > IV > I D) IV > I > II > III
29. Rank the following activating groups in order of decreasing strength of activation,
listing the most activating first.
A) IV > II > III > I C) III > IV > II > I

B) II > III > IV > I D) II > IV > III > I
30. Rank the following deactivating groups in order of increasing deactivating strength,
listing the least deactivating first.
A) I < II < III < IV C) II < I < III < IV

B) II < III < IV < I D) IV < III < I < II
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31. What are the product(s) of the following reaction?
A) Only I B) Only II C) Only I and II D) Only III
32. What are the product(s) of the following reaction?
A) Only I and II B) Only I and III C) Only II and III D) Only IV
33. How can polyalkylation be minimized in Friedel-Crafts alkylation?

A) Use a large excess of alkyl halide relative to the aromatic compound.
B) Use a large excess of benzene relative to the alkyl halide.
C) Use an alkyl halide without a Lewis acid catalyst.
D) Use a large excess of the Lewis acid catalyst.
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36. What are the two distinct pathways for nucleophilic aromatic substitution?
A) Addition-substitution and substitution-addition
B) Addition-elimination and elimination-addition
C) Addition-addition and elimination-elimination
D) Elimination-substitution and substitution-elimination
37. What is the reactive intermediate formed in the addition-elimination mechanism of

nucleophilic aromatic substitution?
A) Carbocation B) Radical C) Benzyne D) Carbanion
38. What is the reactive intermediate formed in the elimination-addition mechanism of

nucleophilic aromatic substitution?
A) Carbocation B) Radical C) Benzyne D) Carbanion
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39. Which of the following statements about nucleophilic aromatic substitution is not true?
A) Increasing the electronegativity of the halogen increases the reactivity of the aryl
halide.
B) Increasing the number of electron-withdrawing groups increases the reactivity of
the aryl halide.
C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower the
energy of the transition state.
D) When a nitro group is located meta to the halogen, the negative charge of the
intermediate carbanion can be delocalized onto the NO2 group, thus stabilizing it.
40. Which of the following statements about nucleophilic aromatic substitution is true?
A) For the addition-elimination pathway, the nucleophile may become attached either
at the site bearing the leaving group or at the site bearing the ortho hydrogen atom.
B) For the elimination-addition pathway, the nucleophile becomes attached only at the
site bearing the leaving group.
C) The elimination-addition mechanism is not as common as the addition-elimination
mechanism.
D) In the addition-elimination mechanism, the aromatic ring first accepts a pair of
electrons from a nucleophile to form a cationic intermediate.
41. Rank the following compounds in order of increasing reactivity in nucleophilic aromatic
substitution.
A) III < II < I B) I < II < III C) III < I < II D) I < III < II
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43. Which aryl fluoride reacts the fastest with NaOH?
44. In addition to the product shown, what other product is formed in the following
reaction?
45. Which set of reagents would most likely bring about the following transformation?
A) Br2 and FeBr3 B) NBS and light C) Br2 in CCl4 D) NaBr and H2O
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49. What is the best choice of reagent to bring about the following transformation?
A) [1] LiAlH4; [2] H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C
50. What is the best choice of reagent to bring about the following transformation?
A) [1] LiAlH4; [2]H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C
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Chapter 19: Carboxylic Acids and the Acidity of the O-H Bond
1. What is the hybridization of the carbon atom in a carboxy group?

A) sp B) sp2 C) sp3 D) p
2. Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an
alcohol?
A) The carbon in the alcohol is sp2 hybridized and has a higher percent s-character that
lengthens the C-O bond in the alcohol.
B) The carbon in the carboxylic acid is sp3 hybridized and has a lower percent s-
character that shortens the C-O bond in the carboxylic acid.
C) The carbon in the carboxylic acid is sp hybridized and has a higher percent s-
D) The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-
3. What two groups make up the carboxylic acid group (RCOOH)?

A) Carbon dioxide and hydrogen C) Carbon monoxide and hydroxyl
B) Carbonyl and hydroxyl D) Carbonyl oxide and hydrogen
4. What is the correct IUPAC name of the following compound?
A) 4-Isopropyl-3-methylbutanoic acid C) 3,5-Dimethylhexanoic acid

B) 2,4-Dimethylhexanoic acid D) 3,5-Dimethy-1-hexanoic acid
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A) 3,5,5-Trimethylcyclohexanecarboxylic acid
B) 3,3,5-Trimethylcyclohexanecarboxylic acid
C) 3,3,5-Trimethylcyclohexanoic acid
D) 3,5,5-Trimethylcyclohexanoic acid
A) 2-sec-Butyl-4,4-dimethylnonanoic acid
B) 4,4-Dimethyl-2-isobutylnonanoic acid
C) 4,4-Dimethyl-2-sec-butylnonanoic acid
D) 2-Isobutyl-4,4-dimethylnonanoic acid
A) 3,4-Dimethylcyclohexanoic acid
B) 3,4-Dimethylcyclohexanecarboxylic acid
C) 4,5-Dimethylcyclohexanecarboxylic acid
D) 1,2-Dimethylcyclohexanecarboxylic acid
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A) -Methylbutyric acid C) -Methylvaleric acid

B) -Propylpropionic acid D) -Methylcaproic acid
A) ,-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid

B) 2,3-Dimethoxyvaleric acid D) ,-Dimethoxycaproic acid
A) ,-Dimethyl--fluorobutyric acid
B) -Fluoro-,-dimethylbutyric acid
C) -Fluoro-,,-trimethylpropionic acid
D) -Fluoro-,,-trimethylbutyric acid
A) Propanedioic acid C) Malonic acid

B) 1,3-propanedicarboxylic acid D) Succinic acid
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A) (E)-2-Hexenoic acid C) (E)-4-Hexenoic acid

B) (Z)-2-Hexenoic acid D) (Z)-4-Hexenoic acid
A) 2-Methoxypentanoic acid C) 4-Methoxybutanoic acid

B) 2-Methoxybutanoic acid D) 4-Methoxypentanoic acid
14. Which of the following is the structure of oxalic acid?
15. Which of the following is the correct IUPAC name for the following structure?
A) Potassium propanoate C) Potassium propanoic

B) Butanoic potassium D) Potassium butanoate
16. Which of the following is the most polar organic compound?

A) CH3CH2CH2CH3
B) CH3CH2CHO
C) CH3CH2CH2OH
D) CH3COOH
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17. Arrange the following compounds in order of increasing boiling point, putting the
compound with the lowest boiling point first.
A) I < II < III < IV C) III < II < IV II > III > IV C) I > II > IV > III

B) I > IV > II > III D) IV > III > II > I
19. Arrange the following compounds in order of increasing water solubility, putting the
least soluble compound first.
A) I < II < III < IV C) I < III < II < IV

B) II < I < III < IV D) IV < II < III < I
20. What two strong absorptions are characteristic of the IR spectrum of carboxylic acids?
A) A C=O absorption at 1710 cm-1 and a C-H absorption at 3000 cm-1.
B) A C=O absorption at 1710 cm-1 and an O-H absorption at 2500-3500 cm-1.
C) A C=O absorption at 1600 cm-1 and an O-H absorption at 2500-3000 cm-1.
D) A C-O absorption at 1500 cm-1 and an O-H absorption at 2500-3500 cm-1.
21. Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra?
A) Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the 
carbon to the carboxy group.
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B) Between 6 and 9 ppm for the OH proton and 2-2.5 ppm for the protons on the 
C) Between 10 and 12 ppm for the OH proton and 1-1.5 ppm for the protons on the 
D) Between 6 and 9 ppm for the OH proton and 1-1.5 ppm for the protons on the 
22. Why is pure acetic acid often called glacial acetic acid?
A) Because it freezes just below 0°C, forming white crystals.
B) Because it freezes just below 100°C, forming white crystals.
C) Because it freezes just below room temperature, forming white crystals.
D) Because it freezes just above room temperature, forming white crystals.
23. Which of the following reagents can accomplish the transformation below?
A) PCC, CH2Cl2 C) [1] O3; [2] H2O

B) [1] LiAlH4, THF; [2] H2O D) K2Cr2O7, H2SO4, H2O
24. What is the other product formed in the oxidation of the following terminal alkyne?
A) HCOOH B) HCOH C) CO2 D) CO
25. Which of the following cannot be the starting material for the following reaction?
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26. In the presence of strong acids, which of the oxygen atoms on the carboxyl group is
preferentially protonated and why?
A) Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is
stabilized by resonance.
B) Protonation occurs at the carbonyl oxygen because the resulting conjugate base is
stabilized by the inductive effect.
C) Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is
stabilized by resonance.
D) Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is
stabilized by the inductive effect.
27. Which of the following structures is the major contributor to the resonance hybrid of the
phenoxide anion?
28. Arrange the following compounds in order of increasing acidity, putting the least acidic
first.
A) I < II < III < IV C) III < IV < II < I

B) IV < III < II < I D) IV < II < III < I
29. Which of the following bases are strong enough to significantly deprotonate ethanol,
CH3CH2OH (pKa = 16)?
A) NaOCH3 B) NaOH C) NaH D) NaOCH2CH3
30. Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least
acidic.
A) Ha < Hb < Hc < Hd C) Hd < Ha < Hc < Hb

B) Hb < Hc < Ha < Hd D) Hb < Hc < Hd < Ha
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first.
A) IV > III > I > II C) II > I > IV > III

B) IV > II > I > III D) II > I > III > IV
first.
A) II < III III > II > I C) I > II > III > IV

B) IV > I > III > II D) IV > II > III > I
first.
A) I < II < III < IV C) IV IV > I > II C) I > II > III > IV

B) IV > III > I > II D) IV > III > II > I
37. What physical property and reaction type are used by extraction as useful techniques to
separate and purify mixtures of compounds?
A) Physical property = solubility differences; reaction type = acid-base reaction.
B) Physical property = boiling point; reaction type = acid-base reaction.
C) Physical property = solubility differences; reaction type = oxidation-reduction.
D) Physical property = density; reaction type = oxidation-reduction.
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38. What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a
separatory funnel containing H2O and CH2Cl2?
A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in
the organic layer.
B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve
in the water layer.
C) Both benzoic acid and NaCl would dissolve in the organic layer.
D) Both benzoic acid and NaCl would dissolve in the water layer.
39. What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2
is treated with aqueous NaOH solution?
A) Benzoic acid would remain in the CH2Cl2 layer, and cyclohexanol would dissolve
in the aqueous layer.
B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would
remain in the CH2Cl2 layer.
C) The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol
would remain in the CH2Cl2 layer.
D) The salt of benzoic acid would remain in the CH2Cl2 layer while cyclohexanol
would dissolve in the aqueous layer.
compound first.
A) III < I < II < IV C) III < II < I < IV

B) IV < I < II < III D) II < IV < I < III
41. What is the overall charge of the amino acid, alanine, at pH = 2?

A) + 1 B) – 1 C) No overall charge D) + 2
A) + 1 B) – 1 C) No overall charge D) – 2

A) + 1 B) – 1 C) No overall charge D) + 2
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44. As applied to the chemistry of amino acids, what is the definition for the isoelectric
point?
A) The pH at which the amino acid exists primarily in its acidic form.
B) The pH at which the amino acid exists primarily in its basic form.
C) The pH at which the amino acid exists as a mixture of isomers.
D) The pH at which the amino acid exists primarily in its neutral form.
Chapter 20: Introduction to Carbonyl Chemistry;

Organometallic Reagents; Oxidation and Reduction
1. What is the name of the general reaction type that aldehydes and ketones undergo?
A) Electrophilic addition C) Nucleophilic substitution
B) Nucleophilic addition D) Electrophilic substitution
2. What is the name of the general reaction type that carboxylic acids, esters, and amides
undergo?
A) Electrophilic acyl addition C) Nucleophilic acyl substitution
B) Nucleophilic acyl addition D) Electrophilic acyl substitution
3. What are the two steps in a nucleophilic addition mechanism?

A) Nucleophilic attack followed by protonation.
B) Nucleophilic attack followed by deprotonation.
C) Nucleophilic attack followed by substitution.
D) Nucleophilic attack followed by elimination.
4. Which of the following terms explain why aldehydes are more reactive than ketones?
A) Electronegativity and resonance C) Electronegativity and hybridization
B) Hybridization and resonance D) Sterics and electronics
5. Why are ketones less reactive than aldehydes?

A) Ketones are more sterically hindered.
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B) Ketones are less electron deficient due to donation from the two alkyl groups.
C) The statement is false; Ketones are more reactive than aldehydes.
D) Both (a) Ketones are more sterically hindered and (b) Ketones are less electron
deficient due to donation from the two alkyl groups.
6. If a compound is reduced, what is the result?

A) Fewer C-H bonds
B) Increased number of C-H bonds
C) Fewer C-Z bonds
D) Both increased number of C-H bonds and fewer C-Z bonds
7. Rank the following compounds in order of decreasing reactivity in nucleophilic addition

reactions, starting with the most reactive compound.
A) III > I > IV > II C) IV > II > III > I

B) II > IV > I > III D) II > IV > III > I
8. Rank the following compounds in order of increasing reactivity in nucleophilic acyl

substitution reactions, starting with the least reactive compound.
A) III < II < I B) II < III < I C) III < I < II D) II < I < III
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12. Which reagent can be used to reduce the alkene in cyclopentenone?

A) NaBH4 B) LiAlH4 C) H2 and Pd-C D) DIBAL-H
13. Which reagent can be used to reduce the carbonyl in methyl vinyl ketone?
A) NaBH4/CH3OH B) H2 and Pd-C C) FeCl3 D) NaH
14. Which reagent can be used to reduce an acid chloride to an aldehyde?

A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3
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15. What reagent would be used to reduce an amide to an amine?

A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3
18. What will be the product of the following reaction (before any aqueous work-up)?
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19. Why would the alcohol in the following compound need to be protected before
reaction?
A) If it isn't protected, the product will be a carboxylic acid.

B) The Grignard reagent will react with the alcohol before the ketone.
C) Magnesium is Lewis acidic and will coordinate with the alcohol.
D) There is no need to protect the alcohol.
20. What is the purpose of a silyl ether?

A) To protect esters from organometallic reagents and other reagents
B) To protect ketones from organometallic reagents and other reagents
C) To protect alcohols from organometallic reagents and other reagents
D) To prevent the formation of carboxylic acids
21. What reagent can be used to cleave a silyl ether protecting group?
A) NaOMe B) MeMgBr C) Bu4NF D) Pd/C
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29. Rank the carbon-metal bond in the following organometallic reagents in order of
decreasing polarity, starting with the most polar.
A) II > I > III B) II > III > I C) III > I > II D) III > II > I
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30. Which of the following statements about organometallic reagents is not true?
A) Organometallic reagents contain a carbon atom bonded to a metal.
B) The more polar the carbon-metal bond, the more reactive the organometallic
reagent.
C) Organometallic reagents react as bases and nucleophiles.
D) Organometallic reagents are strong acids that readily donate a proton to water.
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34. What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?
35. What is the major organic product in the following sequence of reactions?
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38. What is the major organic product in the following sequence of reactions?
39. What is the missing reagent in the reaction below?
A) [1] Mg, [2] CO2, [3] acidic work-up C) [1] CO2, [2] acidic work-up
B) [1] CO2, [2] NaOH D) LiAlH4
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A) Et2CuLi then H2O

B) EtMgBr then H2O
C) NaBH4/CH3OH
D) H2, Pd-C
A) PhMgBr then H2O C) Ph2CuLi then H2O

B) Benzene, AlCl3 D) PhLi then H2O
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A) NaBH4/CH3OH
B) H2, Pd-C
C) LiAlH4 then H2O
D) MeMgBr then H2O
46. What is the starting material in the reaction below?
A) Bromobenzene
B) Benzyl bromide
C) Benzoic acid
D) Lithium benzoate
A) NaBH4/CH3OH B) DIBAL-H C) H2, Pd-C D) LiAlH4 then H2O
48. Rank the following compounds in order of increasing reactivity toward the nucleophilic
hydride reagent, NaBH4.
A) I < II < III B) III < II < I C) II < III < I D) II < I < III
49. A carbonyl group, C=O, and an alkene, C=C, double bonds, are both sp2 hybridized.
However, the chemistry of these two functional groups is very different. This can be
explained by which of the following statements?
A) The bond angle of the carbonyl is larger than the bond angle of the alkene.
B) The electronegative oxygen of the C=O group makes this bond polar.
C) The bond of the C=C is longer that the bond of the C=O.
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D) There is more steric crowding in the carbonyl than in the alkene.
50. Both LiAlH4 and NaBH4 are reducing agents. Which statement about these reagents is
true?
A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
greater than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing
agent.
B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
greater than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.
C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
less than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent.
D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
less than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.
51. If the starting material has no stereogenic centers, when carbonyl compounds are
reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is
formed, what will the composition of the product mixture be?
A) Forms a racemic mixture of the two possible enantiomers
B) Forms more of one enantiomer than another because of steric reasons around the
carbonyl
C) Forms more of one enantiomer than another depending on the temperature of the
reaction
D) Forms different products depending on the solvent used
52. Rank the following compounds in order of increasing reactivity (least to most reactive)
with respect to acyl substitution.
I. methyl benzoate
II. benzoylchloride
III. benzamide
A) III< I < II B) II < I < III C) II < III < I D) I < III < II
53. The behavior of acid chlorides is different from that of aldehydes in a reaction with a
nucleophile because
A) The acid chloride contains a better leaving group.
B) The aldehyde is more easily oxidized.
C) The carbonyl of the aldehyde is more positive.
D) The carbonyl of the aldehyde is less hindered.
Chapter 21: Aldehydes and Ketones – Nucleophilic Addition
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1. Which is the most reactive carbonyl compound?
A) pivaldehyde C) tert-butyl aldehyde

B) 2,2-dimethylpropanal D) 2,2-dimethylpentanal
3. What is the structure of 3-methylcyclohexanone?
4. What is the structure of 2-trifluoromethyl-2-methoxybutanal?
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5. What is the structure of benzophenone?
6. Using IR spectroscopy, how can you tell the difference between a ketone and an
aldehyde?
A) A ketone has no carbonyl stretch at 1720 cm-1.
B) An aldehyde has a carbonyl stretch at 1820 cm-1.
C) An aldehyde has two C-H stretches between 2700-2850 cm-1.
D) A ketone has no C-H stretches.
7. Which of the following will have the highest wave number for the carbonyl stretch in
the IR spectrum?
8. Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a
ketone?
A) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm-1.
B) An aldehyde has a proton signal between 9-10 ppm.
C) A ketone has signals around 2-3 ppm.
D) A ketone has a signal around 200 ppm.
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9. What compound is consistent with the following 1H NMR spectrum?
A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone
10. Which of the following oxidants would work for the following reaction?
A) H2Cr2O7 B) FeCl3 C) I2 D) Ag2O
11. What is the first step in nucleophilic addition under acidic conditions?
A) Protonation of the nucleophile C) Loss of water
B) Addition of the nucleophile D) Protonation of the carbonyl
12. Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition
of a Grignard reagent to a ketone?
A) Because the Grignard reagent will react with the acid and be quenched.
B) Because the ketone will be protonated and thus unreactive.
C) Because the ketone will form an unreactive enol.
D) Because the Grignard reagent won't dissolve in aqueous solutions.
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14. Is the following reaction reversible and, if so, under what conditions?
A) No C) Yes, using Pd/C

B) Yes, under acidic conditions D) Yes, under basic conditions
15. What would you use to prepare the following ylide from the starting phosphonium salt?
A) butyl lithium C) triphenylphosphine

B) 1-bromo-2-methylpropane D) acetic acid
16. What is the driving force for the Wittig reaction?

A) The formation of an alkene
B) The deprotonation of a phosphonium salt
C) The elimination of triphenylphosphine oxide
D) The formation of a phosphonium salt
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18. Why are strongly acidic conditions not used in the formation of enamines and imines?
A) The carbonyl will be protonated.
B) The amine will be completely protonated.
C) The product is not stable to strong acid.
D) An enol will be formed.
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21. What needs to be done to make the following reaction proceed?
A) Heat the reaction.

B) Add an acid catalyst only.
C) Add a base catalyst only.
D) Heat the reaction and add an acid catalyst.
22. What needs to be done to make the following reaction go to starting materials?
A) Heat the reaction. C) Add aqueous base.

B) Add aqueous acid. D) Add water.
23. What sequence of reactions is required for the following transformation?
A) [1] NaOMe, [2] acetone C) [1] Ph3P, [2] KOtBu, [3] acetone
B) [1] Ph3P, [2] acetone D) acetone, heat
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24. What is the product?
A) I only B) II only C) III only D) II and III
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A) I only B) II only C) III only D) II and III
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A) Ethyl amine, mild acid C) Diethylamine, strong acid

B) Diethylamine, mild acid D) Diethylamine, NaOMe
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33. What is the cyclic hemiacetal product formed from intramolecular cyclization of the
following hydroxy aldehyde?
A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe
35. Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO
with Ph3P CHCH3?
36. What is the IUPAC for the following compound?
A) 1-formyl-2-nitropropane C) 2-nitrobutanal
B) 1-formyl-3-nitrobutane D) 3-nitrobutanal
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38. How would the following compounds be distinguishable using IR and 1H NMR
spectroscopy?
A) The 1H NMR spectrum of compound I will have two singlets.

B) The C=O absorption in the IR spectrum of compound I will be at a higher wave
number than that of compound II.
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of
about 4.
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O
absorption in the IR spectrum of compound I will be at a higher wave number than
that of compound II.
39. Name the following aldehyde.
A) 1-methylcyclopentanal C) 2-methylcyclopentanecarbaldehyde
B) 2-methylcyclopentanal D) 1-methylcyclopentanylcarbaldehyde
40. Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling
point of 118 °C. What accounts for this difference in boiling points?
A) Butanol is polar while butanal is not polar.
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B) Butanol can exhibit dipole-dipole interactions while butanal cannot.

C) Butanol can hydrogen bond and butanal cannot hydrogen bond.
D) Butanal is less sterically hindered than butanol.
41. Identify how you could synthesize an enamine.

A) React a ketone or an aldehyde with a secondary amine.
B) React a ketone or an aldehyde with a primary amine.
C) React a ylide with a primary amine.
D) React a ylide with a secondary amine.
42. When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the
product called?
A) Hemiacetal B) Di-ether C) Di-alkoxy alkane D) Acetal
43. Cyclic acetals are used as protecting groups for ketones or aldehydes because they are
inert to all of the following reagents except
A) aqueous acid. C) oxidizing reagents.
B) aqueous base. D) reducing reagents.
44. Which of the following statements about carbohydrates is not true?

A) Carbohydrates are sugars and starches.
B) Carbohydrates often contain acetals and hemiacetals.
C) In solution, glucose is in the cyclic acetal form only.
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.
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Chapter 22: Carboxylic Acids and Derivatives
1. Which of the following is a lactam?
2. Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?
A) Nitrogen is a better leaving group.
B) Chloride is a better leaving group.
C) Nitrogen donates more electron density into the carbonyl.
D) The amide anion is less basic.
A) methyl 3-methylbutanamide C) N-methyl 3-methylhexanamide
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B) 5-methylhexanamide D) N-methyl 3-methylbutanamide
A) 4-fluoro-3-methylbenzoate C) 3-methyl-4-fluorobenzoic acid

B) 4-fluoro-3-methylbenzoic acid D) 4-fluoro-5-methylbenzoic acid
5. What is the structure for acetic propanoic anhydride?
6. What is the structure for ethyl 4-chlorobenzoate?
7. What is the structure for 3-cyanocyclopentanone?
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A) 2-fluorobutanonitrile C) 3-fluoropentanonitrile
B) 2-fluoropentanonitrile D) 2-fluorobutylcyanide
9. Where is the carbonyl absorption found in the IR spectrum of a simple ester?

A) 2.5 ppm B) 2250 cm-1 C) 3800 cm-1 D) 1740 cm-1
10. Which of the following peaks would you see in the IR spectrum of a carboxylic acid?
A) A flat line (carboxylic acids are not IR active)
B) A sharp line at 2250 cm-1
C) A broad peak from 3800-2800 cm-1
D) A broad peak from 800-600 cm-1
11. You see an absorption at 2250 cm-1 in the IR spectrum of a compound. What kind of
functional group is present?
A) A ketone B) An aldehyde C) An ester D) A nitrile
12. Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid
derivatives?
A) 1700 cm-1 B) 180-160 ppm C) 2.5-3.0 ppm D) 100-80 ppm
13. Which structure is consistent with the following 1H NMR spectrum?
A) ethyl acetate C) 3,3-dimethyl-2-pentanone
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B) 2-propanone D) ethyl 2,2-dimethylpropionate
14. What is the first step in the general mechanism for nucleophilic acyl substitution?
A) Protonation of the carbonyl
B) Removal of an -proton
C) Addition of the nucleophile to the carbonyl
D) Loss of the leaving group
15. Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate?
A) The nucleophile is too basic.
B) Reforming the carbonyl is energetically favorable.
C) The leaving group is unstable and wants to be negatively charged.
D) There is no tetrahedral intermediate.
16. Will the following reaction occur?
A) Yes B) No
A) Yes B) No
A) Yes B) No
19. Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?
A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile.
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B) Pyridine will neutralize the acid by-product of the reaction.

C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive.
D) Pyridine will absorb the heat of the reaction.
22. How can you convert a carboxylic acid into an ester?

A) Heat with an alcohol and catalytic acid
B) Deprotonate with a base and react with an alcohol
C) Deprotonate with a base and react with an alkyl halide
D) Both (a) heat with an alcohol and catalytic acid and (c) deprotonate with a base and
react with an alkyl halide
E) Both (a) heat with an alcohol and catalytic acid and (b) deprotonate with a base and
react with an alcohol
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23. How can you convert a carboxylic acid into an acid chloride?
A) Heat with hydrochloric acid C) React with sodium chloride
B) React with thionyl chloride (SOCl2) D) React with Cl2 and FeCl3
25. What is the direct product of the base-promoted hydrolysis of an ester?

A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt
26. Which of the following two amides will react more readily with a nucleophile? Why?
A) I, because it is less hindered C) I, because it is more strained

B) II, because it is less hindered D) II, because it is more strained
A) Hexanoic acid B) 1-Hexanamide C) Hexanal D) 1-Hexanamine
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28. What is the product of the following reaction (after acidic work-up)?
29. What reagent would you use for the following transformation?
A) LiAlH4 B) DIBAL-H C) NaBH4 D) H2, Pd/C
30. What is the structure for the compound whose IUPAC name is pentyl 2-
methylbutanoate?
A) Propionyl phenol C) Phenol propanoate

B) Phenyl propanoate D) Phenyl acetate
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A) acetic acid B) NaOMe C) SOCl2 D) pyridine
39. Which of the following reaction conditions can be used to synthesize an ester
(RCOOR')?
A) RCOCl + R'NH2 + pyridine C) RCOOH + R'OH + OH-
B) RCOOH + R'OH + H+ D) RCONH2 + R'OH
40. Rank the following compounds in order of increasing reactivity in nucleophilic acyl
substitution.
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
41. Draw the structure of N-phenyl acetamide.
42. Which of the following substrates cannot be used as an immediate precursor to

synthesize an ester?
43. From the list below, pick the compound that does not react with acetyl chloride.
A) Isopropyl alcohol B) Benzoic acid C) Ammonia D) Triethyl amine
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44. Which of the following statements about amides is true?

A) Amides react with methyl alcohol in the presence of an acid catalyst to form an
ester.
B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate
anions.
C) Amides react with thionyl chloride to form the acid chloride.
D) Amides do not react under any conditions. They are inert compounds.
45. n-Butanenitrile will undergo all of the following listed reactions except one. Which
reaction listed is not true for n-butanenitrile?
A) n-Butane nitrile will react with ethylmagnesium bromide to form an alcohol.
B) n-Butanenitrile with be reduced to butyl amine in the presence of LiAlH4 with an
aqueous work-up.
C) n-Butanenitrile is hydrolyzed in the presence of acid to form butanoic acid.
D) n-Butanenitrile is reduced with DIBAL-H to form n-butanal.
46. An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown
compound is probably
A) an alkane B) an aldehyde C) an alkene D) a nitrile
47. All of the following contain sp2 hybridized atoms in their functional group except
A) a carboxylic acid B) a nitrile C) an aldehyde D) an anhydride
Chapter 23: Substitution Reactions of Carbonyl Compounds at

the Alpha-Carbon
1. Which is the more stable form of acetophenone?
A) Only I B) Only II C) Only III D) I and II are equally stable
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2. Which is the most stable form of 1,3-cyclohexanedione?
3. Which of the following is an enol form of the following compound?
4. Why is the enolate of acetone less basic than the allyl anion derived from propene?
A) Because there are more atoms in acetone
B) Because there are more resonance structures for the enolate of acetone
C) It isn't; the allyl anion is less basic.
D) One of the resonance structures for the enolate places the negative charge on the
more electronegative oxygen.
5. Which of the following four compounds is the most acidic?
6. Will acetone be completely deprotonated by potassium tert-butoxide?

A) Yes B) No
7. Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?

A) Yes B) No
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8. Which is the kinetic enolate of 2-methylcyclohexanone?
9. If you want to form a thermodynamic enolate, you want to:

A) Keep the reaction as cold as possible. C) Use a protic solvent such as ethanol.
B) Use an aprotic solvent such as THF. D) Use a carboxylic acid.
10. If you want to form a kinetic enolate, you want to:

A) Use a strong, non-nucleophilic base such as LDA.
B) Use a protic solvent.
C) Use a low temperature.
D) Both use a strong, non-nucleophilic base such as LDA and use a low temperature.
11. Which of the following is the intermediate for halogenation of ketones under acidic
conditions?
A) An enolate B) An enol C) A tautomer D) An epimer
12. Why is it difficult to stop the halogenation of ketones under basic conditions at the
mono-halogenated stage?
A) The ketone undergoes a Bayer-Villigar oxidation.
B) The ketone is reduced.
C) The ketone undergoes an Aldol reaction.
D) The bromine helps to stabilize the second enolate, making the product more acidic
than the starting material.
13. Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?
A) Because tert-butyl bromide is too basic.
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B) Because tert-butyl bromide cannot undergo an SN2 reaction.

C) Because tert-butyl bromide is a nucleophile.
D) Because tert-butyl bromide is not a stable compound.
14. What are the three steps in the malonic ester synthesis?
A) Deprotonation, alkylation, hydrolysis/decarboxylation
B) Hydrogenation, alkylation, deprotonation
C) Alkylation, hydrolysis/decarboxylation. hydrogenation
D) Hydrolysis/decarboxylation, deprotonation, alkylation
15. What is the missing reagent for the following reaction?
A) Br2/HOAc B) Br2/KOH C) Cl2/FeCl3 D) Br2/FeBr3
16. Starting with cyclohexanone, how could you prepare the diketone below?
A) Treat cyclohexanone with a base under thermodynamic conditions.

B) Hydrogenate cyclohexanone with Raney nickel.
C) Convert cyclohexanone into the -bromoketone and then react this with the enolate
of cyclohexanone.
D) Convert cyclohexanone into an enamine with diethylamine and then react this with
more cyclohexanone.
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A) Only I B) Only II C) Only III D) Only I and III
A) Br2/AcOH B) I2/KOH C) I2 D) KOH
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22. What is the starting material for the following reaction?
23. Which of the following compounds is an enol of compound X drawn below?
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24. Which of the following are enol forms of ethyl acetoacetate drawn below?
A) Only I B) Only II C) Only III D) I, II, and III
25. For most compounds with a single keto group in the molecule, equilibrium favors the
keto form over the enol form of the compound. This is due largely to what?
A) The C=O bond is much stronger than the C=C bond.
B) The C=C bond is much stronger than the C=O bond.
C) The keto form can undergo intramolecular hydrogen bonding.
D) The enol form can undergo intramolecular hydrogen bonding.
26. It has been found that -dicarbonyl compounds have a greater concentration of the enol
form over the keto form. This can be explained by:
A) The C=C of the enol is conjugated with the carbonyl group.
B) The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl
group.
C) Both A and B above are true.
D) None of the choices are true.
27. The reaction below is a direct enolate alkylation. It has been found that this reaction
only works well with unhindered methyl and 1° alkyl halides. Pick the statement that
best explains this observation.
A) The nucleophilic enolate requires a reaction center that has a positive charge.
B) Hindered alkyl halides do not undergo SN1 reactions.
C) Hindered alkyl halides do not undergo SN2 reactions.
D) Methyl and 1° alkyl halides can form carbocations that can readily react with the
nucleophilic enolate.
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28. The following molecule is called:
A) a 1,3-diketopentanoate. C) an ethyl acetoacetate.

B) a diethyl malonate. D) a -keto ester.
29. A simple chemical test to distinguish between acetone and 3-pentanone would be the
reaction of the compounds with
A) bromine with acetic acid.
B) bromine and aqueous hydroxide ion.
C) THF, LDA at -78 °C followed by reaction with bromine.
D) base and methyl bromide.
30. Which is the thermodynamic enolate of 2-methylcyclohexanone?
31. Which of the following compounds is the most acidic?

A) Ethyl acetoacetate B) 2-Butanone C) 1-Butanol D) 3-Pentanone
32. Which is the most acidic proton in the following compound?
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33. Which is the most acidic proton in the following compound?
34. Which of the following bases will completely convert 1,4-cyclohexandione into an
enolate?
A) Sodium hydroxide C) Sodium tert-butoxide
B) Sodium methoxide D) Sodium hydride
35. Which of the following compounds would undergo racemization in the presence of a
base?
36. Which of the following ketones will give a positive iodoform test?
A) 3-Heptanone B) 2-Pentanone C) 3-Hexanone D) Cyclohexanone
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38. Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X

(C7H14O) as the major product. X shows a strong absorption in the IR spectrum at 1713
cm-1, and its 1H NMR data is given below. What is the structure of X?
39. The malonic ester synthesis can be adapted to synthesize -amino acids by using diethyl
acetamidomalonate as the starting material. Select the structure of the amino acid
produced by the following synthesis.
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40. Select the appropriate sequence of reactions to accomplish the following synthesis.
A) [1] Br2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br

B) [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br
C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA
41. What is the starting material required to accomplish the following transformation?
Chapter 24: Carbonyl Condensation Reactions
1. What is the general name for the reaction product formed in an aldol addition reaction?
A) -hydroxy carbonyl compound. C) -hydroxy carbonyl compound.
B) -hydroxy carbonyl compound. D) ,-hydroxy carbonyl compound.
2. In the correct order, what are the three steps in the mechanism of an Aldol reaction?
A) Protonation, enolate formation, nucleophilic addition.
B) Enolate formation, protonation, nucleophilic addition.
C) Enolate formation, nucleophilic addition, protonation.
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D) Nucleophilic addition, enolate formation, protonation.
3. Which of the following statements about Aldol reactions with either aldehydes or
ketones is true?
A) Equilibrium favors the products with aldehydes; equilibrium favors the starting
materials with ketones.
B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the
products with ketones.
C) Equilibrium favors the products with both aldehydes and ketones.
D) Equilibrium favors the starting materials with both aldehydes and ketones.
4. What reaction type is an Aldol reaction?

A) nucleophilic substitution C) electrophilic addition
B) electrophilic substitution D) nucleophilic addition
5. What is the Aldol addition product formed from reaction of the following compound
with itself?
6. What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with
itself?
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7. What is the Aldol addition product formed from the reaction of acetone, (CH3)2CO, with
itself?
8. Which of the following carbonyl compounds will undergo Aldol addition reactions
when treated with aqueous sodium hydroxide?
A) I B) II C) III D) None of the choices
9. Which of the following carbonyl compounds do not undergo Aldol addition reactions
when treated with aqueous sodium hydroxide?
10. Why is the Aldol reaction often called an Aldol condensation?

A) The initially formed -hydroxy carbonyl compound loses a hydroxyl group.
B) The initially formed -hydroxy carbonyl compound loses an oxygen atom.
C) The initially formed -hydroxy carbonyl compound loses a hydrogen atom.
D) The initially formed -hydroxy carbonyl compound loses water.
11. What is the general name for the class of products formed in an Aldol condensation
reaction?
A) ,-unsaturated carbonyl compound C) ,-unsaturated carbonyl compound
B) ,-unsaturated carbonyl compound D) -hydroxy carbonyl compound
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12. Which is the unsaturated carbonyl compound is formed by the dehydration of the
following -hydroxy carbonyl compound?
A) I B) II C) I and II D) None of the choices
13. Which is the unsaturated carbonyl compound formed in the dehydration of the following
-hydroxy carbonyl compound?
A) I B) II C) I and II D) None of the choices
14. What aldehyde or ketone is needed to prepare the following compound by an Aldol
reaction?
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15. What is the name given to an Aldol reaction between two different carbonyl
compounds?
A) multiple Aldol reaction C) differential Aldol reaction
B) crossed Aldol reaction D) versatile Aldol reaction
16. When is a crossed Aldol reaction said to be synthetically useful?

A) When both carbonyl compounds have  hydrogens.
B) When both carbonyl compounds have no  hydrogens.
C) When one carbonyl compound has no  hydrogens.
D) When one carbonyl compound has no  hydrogens.
17. In what situation can the yield of a single crossed Aldol product be increased?
A) The electrophilic carbonyl component is relatively unhindered and is used in
excess.
B) The electrophilic carbonyl carbon component is relatively hindered and is used in
limited amount.
C) The nucleophilic carbonyl component is relatively unhindered and is used in
excess.
D) The nucleophilic carbonyl component is relatively hindered and is used in limited
amount.
18. What is the cyclic product formed in the intramolecular Aldol condensation when the
following compound is treated with aqueous NaOH?
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19. What cyclic product is formed in the intramolecular Aldol condensation when the
following compound is treated with aqueous NaOH?
20. What is the general name for the reaction product formed in a Claisen reaction?
A) -hydroxy ester B) -keto ester C) -keto ester D) -hydroxy ester
21. What reaction type is a Claisen reaction?

A) Electrophilic addition C) Nucleophilic addition
B) Electrophilic substitution D) Nucleophilic substitution
22. What type of esters can undergo Claisen reactions?

A) All esters can undergo Claisen reactions.
B) Only esters with two hydrogen atoms on the  carbon can undergo Claisen
reactions.
C) Only esters with three hydrogen atoms on the  carbon can undergo Claisen
reactions.
D) Only esters with two or three hydrogen atoms on the  carbon can undergo Claisen
reactions.
23. What is the product of the following Claisen reaction?
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24. What is the product of the following Claisen reaction?
25. What is the name given to the Claisen reaction between two different esters?
A) multiple Claisen reaction C) crossed Claisen reaction
B) differential Claisen reaction D) versatile Claisen reaction
26. When is a crossed Claisen reaction between two different esters synthetically useful?
A) When only one of the esters has  hydrogen atoms.
B) When both esters have  hydrogen atoms.
C) When only one of the esters has  hydrogen atoms.
D) When both esters lack  hydrogen atoms.
27. What is the general name of the product of a crossed Claisen reaction between a ketone
and an ester?
A) -keto ester C) -dicarbonyl compound
B) ,-dicarbonyl compound D) -dicarbonyl compound
28. In the correct order, what are the three general steps in the mechanism of a Claisen
reaction?
A) Enolate formation, elimination, nucleophilic addition.
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B) Enolate formation, nucleophilic addition, elimination.

C) Elimination, enolate formation, nucleophilic addition.
D) Nucleophilic addition, enolate formation, elimination.
29. What is an intramolecular Claisen reaction called?

A) Michael reaction C) Hoffman reaction
B) Robinson reaction D) Dieckmann reaction
30. In a Michael reaction, what is the name given to the ,-unsaturated carbonyl
component?
A) Michael donor C) Michael nucleophile
B) Michael enolate D) Michael acceptor
31. In a Michael reaction, where does the nucleophile attack the ,-unsaturated carbonyl
component?
A) -Carbon C) Carbonyl carbon
B) -Carbon D) Carbonyl carbon and -carbon
32. Which of the following compounds cannot serve as a Michael acceptor?
33. What are the two starting materials for a Robinson annulation?
A) an ,-unsaturated carbonyl compound and an enolate
B) a -ketoester and an enolate
C) a 1,5-dicarbonyl compound and an enolate
D) a 1,3-dicarbonyl compound and an enolate
34. What are the names for the two parts of the mechanism in a Robinson annulation?
A) Michael addition and intramolecular Claisen reaction
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B) Michael addition and intramolecular aldol reaction

C) Claisen reaction and intramolecular aldol reaction
D) Aldol reaction and intramolecular Claisen reaction
35. Which of the following compounds can undergo an Aldol with itself?
A) I B) II C) III D) Both I and II
36. What is the product of the self-condensation of ethanal (acetaldehyde), shown below?
37. The following reaction is an example of what type of reaction?
A) Claisen condensation C) Robinson annulation

B) mixed Aldol reaction D) Dieckmann condensation
38. The following reaction is an example of what type of reaction?
A) Michael reaction C) Dieckmann condensation
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B) Aldol self-condensation D) Robinson annulation
39. The -hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated
product, what is the explanation for this result?
A) It undergoes elimination, since water is a good leaving group.
B) The hydroxy group is oxidized to a carbonyl.
C) The hydroxy group reacts with the carbonyl to form a ketal.
D) Hydroxide is eliminated via an enolate intermediate.
40. Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is
the reason for this difference in reactivity?
A) The initial Aldol product is an alkoxide, so the reaction is not energetically
downhill in either direction.
B) The initial Aldol product is an alkoxide, so the reaction is energetically downhill
going toward the product.
C) The initial Aldol product is an alkoxide, so the reaction is energetically downhill
going toward the starting materials.
D) Water is a stable molecule.
41. Would this crossed Aldol reaction work well? Why or why not?
A) Yes, the diketone is significantly more acidic, so this enolate can be formed
selectively.
B) Yes, the aldehyde is significantly more acidic, so this enolate can be formed
selectively.
C) No, the aldehyde is significantly more acidic, so this enolate cannot be formed
selectively.
D) No, the diketone is significantly more acidic, so this enolate cannot be formed
selectively.
42. Of the carbonyl compounds; (1) benzaldehyde, (2) acetophenone and (3) dicyclohexyl
ketone, which compound has no -hydrogens?
A) benzaldehyde
B) acetophenone
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C) acetone
D) All of these compounds contain -hydrogens
43. Complete this statement: A major difference between the Aldol condensation and the
Claisen condensation reactions is that
A) the Aldol reaction involves substitution while the Claisen reaction involves
addition.
B) the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed.
C) the Aldol reaction is base catalyzed while the Claisen reaction requires a full
equivalent of base.
D) the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed.
44. If a Claisen condensation reaction is run using methyl propanoate as the reactant,
NaOCH3 is the ideal base. Why is it important to use NaOCH3 and not NaOCH2CH3?
A) NaOCH3 is a stronger base than NaOCH2CH3, and this reaction requires a stronger
base.
B) NaOCH3 is a weaker base than NaOCH2CH3, and this reaction requires a weaker
base.
C) Transesterfication can occur when esters react, and this transesterfication would
result in a mixture of products.
D) NaOCH3 is more soluble than NaOCH2CH3 in organic solvents, and this reaction
requires a full equivalent of base to proceed. A full equivalent of NaOCH2CH3
would not dissolve, so the reaction would not proceed.
45. There are several variations of the Aldol reaction. Which of the following types of
reactants leads to only one possible product with the Aldol condensation reaction?
A) Two different aldehydes with -hydrogens are able to form a single aldol
condensation product.
B) Two different ketones with -hydrogens are able to form a single aldol
condensation product.
C) Any aldehyde and ketone mixed together can react to form a single condensation
product.
D) Any pair of aldehyde or ketone reactants where one of the reactants has no -
hydrogens will lead to a single aldol product.
Chapter 25: Amines
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1. Which of the following amines are classified as primary (1°) amines?
2. Which of the following amines are classified as secondary (2°) amines?
3. Which of the following amines are classified as tertiary (3°) amines?
4. What is the approximate bond angle of the substituents around a nitrogen atom in
amines?
A) 90° B) 109.5° C) 120° D) 180°
5. Although an amine nitrogen atom containing an electron pair and bonded to three
different groups is technically a stereogenic center, the chirality of the amine nitrogen is
often ignored. Why is that?
A) Because four bonds are needed to define a stereogenic center.
B) Because chirality only exists with the tetrahedral carbon atoms.
C) Because there is usually slow interconversion between the two isomeric forms at
room temperature.
D) Because there is usually rapid interconversion between the two isomeric forms at
room temperature.
6. Why should the chirality of an ammonium salt with four different groups on the
nitrogen atom not be ignored?
A) Because there is rapid interconversion between the two isomeric forms at room
temperature.
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B) Because interconversion cannot occur between the two isomeric forms at room
temperature.
C) Because the compound would be a meso compound.
D) Because the compound would be a racemic mixture.
A) isopropylamine C) 2-methyl-1-propanamine
B) sec-butylamine D) isobutylamine
A) isopropylamine
B) sec-butylamine
C) isobutylamine
D) tert-butylamine
A) isopropylamine C) tert-butylamine
B) 2-methyl-2-propanamine D) isobutylamine
A) diisopropylamine
B) dipropylamine
C) diisopropanamine
D) dibutylamine
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A) dimethylisobutylamine C) N,N-dimethylbutanamine
B) butyldimethylamine D) sec-butyldimethylamine
A) N-propylhexanamine C) N-ethylcyclohexylamine
B) N-propylaniline D) N-propylcyclohexanamine
A) N-ethyl-N-methylpentylamine C) N-methyl-3-octanamine
B) N-ethyl-N-methyl-1-pentanamine D) N-ethyl-2-heptanamine
A) 3-methyl-1-hexanamine C) 4-methyl-1-hexanamine
B) 4-methyl-1-hexylamine D) 3-methyl-6-hexylamine
A) N-ethyl-N-methylcyclopentanamine C) N-methyl-N-ethylcyclopentylamine
B) N-cyclopentyl-N-methylethanamine D) N-ethyl-N-methylpentanamine
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A) 1-methyl-N-propyl-1-propanamine C) 2-propyl-3-hexanamine
B) 4-methyl-4-heptanamine D) N-propyl-2-pentanamine
A) (S)-methyl-4-hexanamine C) (R)-2-methyl-4-hexanamine
B) (S)-5-methyl-3-hexanamine D) (R)-5-methyl-3-hexanamine
A) (Z)-4-hexen-1-amine C) (E)-2-hexen-6-amine
B) (E)-4-hexen-1-amine D) (Z)-2-hexen-6-amine
19. What is the correct assignment of the names of the following aromatic amines?
A) I = pyrrolidine; II = pyrimidine; III = aniline.

B) I = pyrrole; II = pyrimidine; III = anisole.
C) I = pyrrolidine; II = pyridine; III =aniline.
D) I = pyrrole; II = pyridine; III = aniline.
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20. Arrange the following compounds in order of decreasing boiling point, putting the
A) I > II > III B) I > III > II C) III > I > II D) III > II > I
21. Arrange the following compounds in order of increasing boiling point, putting the
compound with the least boiling point first.
A) I < II < III B) II II > III B) II > I > III C) III > I > II D) II > III > I
23. The mass spectrum of an amine shows a parent peak with an odd mass for the molecular
ion. What does this tell you about the amine?
A) The amine is a primary amine.
B) The amine is a secondary amine.
C) The amine contains an even number of N atoms.
D) The amine contains an odd number of N atoms.
24. What is a typical characteristic absorption in the IR spectrum of a primary amine?

A) Two N-H absorptions at 2500-2600 cm-1
B) One N-H absorption at 2500-2600 cm-1
C) Two N-H absorptions at 3300-3500 cm-1
D) One N-H absorption at 3300-3500 cm-1
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25. A compound with molecular formula C6H15N exhibits a singlet at  0.9 (1H), a triplet at
 1.10 (3H), a singlet at  1.15 (9H), and a quartet at  2.6 (2H) in its 1HNMR spectrum.
Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the
structure of this compound?
26. What is the name given to naturally occurring amines derived from plant sources?
A) Enamines B) Imines C) Alkaloids D) Alkamines
27. Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful
method for preparing primary amines?
A) NH3 is not a nucleophile.
B) Elimination will occur.
C) NH3 is too bulky to act as a nucleophile.
D) Polyalkylation of the amine will result in multiple products.
28. In the preparation of primary amines, how can direct nucleophilic substitution between
NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a
1:1 ratio?
A) Use a large excess of NH3.
B) Use a large excess of alkyl halide.
C) Use a limited amount of NH3.
D) Make the alkyl halide sterically hindered.
29. Why is the N-H bond of an imide especially acidic?

A) The conjugate base is stabilized by electron-donating inductive effect.
B) The conjugate base is stabilized by resonance.
C) The conjugate acid is stabilized by resonance.
D) The conjugate base is stabilized by intramolecular hydrogen bonding.
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30. Which of the following alkyl halides cannot be used to prepare primary amines by the
Gabriel synthesis?
A) 2-bromo-2-methylbutane C) 2-bromo-3-methylbutane
B) 1-bromo-2-methylbutane D) 1-bromo-3-methylbutane
31. Predict the product(s) of the following reaction.
A) I B) II C) III D) None of the choices
32. What is the major organic product obtained in the following reaction?
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36. Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?
A) Because of the electron-withdrawing inductive effect of the alkyl groups.
B) Because of the steric hindrance of the alkyl groups.
C) Because of the resonance delocalization of the alkyl groups.
D) Because of electron-donating inductive effect of the alkyl groups.
37. Why are alkylamines more basic than arylamines?

A) The lone pair electrons are localized in alkylamines and delocalized in arylamines.
B) The lone pair electrons are delocalized in alkylamines and localized in arylamines.
C) The lone pair electrons are less readily available in alkylamines.
D) The lone pair electrons are more readily available in arylamines.
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38. Rank the following compounds in order of increasing basicity, putting the least basic
compound first.
A) III < II < IV I > III > IV C) I > III > II > IV

B) I > II > III > IV D) IV > II > III > I
40. Rank the following compounds in order of increasing basicity, putting the least basic
first.
A) II < III < IV II > III > IV C) IV > III > I > II
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B) I > III > II > IV D) II > I > III > IV
42. Why is pyrrole much less basic than pyridine?

A) The lone pair of electrons in pyrrole is located on an sp2 orbital.
B) The lone pair of electrons in pyrrole is part of the aromatic  system.
C) The lone pair of electrons in pyrrole is not part of the aromatic  system.
D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of
pyridine.
43. Why is piperidine a stronger base than pyridine?

A) The lone pair of electrons in pyridine is part of the delocalized  system.
B) Aromatic compounds are always less basic than non-aromatic compounds.
C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of
electrons in pyridine is in an sp hybrid orbital.
D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of
electrons in pyridine is in an sp2 hybrid orbital.
44. Rank the following compounds in increasing order of basicity, putting the least basic
first.
A) II < I < IV < III C) IV < II < III N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2
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46. Histamine, a vasodilator, is responsible for a wide variety of physiological effects. Rank
the three nitrogen atoms in histamine in increasing order of basicity, putting least basic
nitrogen atom first.
A) N2 < N1 < N3 B) N1 < N2 < N3 C) N3 < N1 < N2 D) N3 < N2 < N1
47. Predict the major organic product of the following reaction.
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53. Select the reagent(s) required for the following transformation.
A) NaI B) (1) NaNO2, HCl; (2) NaI C) (1) NaNO2, HCl; (2) I2 D) I2
A) NaF B) (1) NaNO2, HCl; (2) F2 C) (1) NaNO2, HCl; (2) HBF4 D) F2
A) (1) NaNO2, HCl; (2) H2 C) (1) NaNO2, HCl; (2) H3PO4

B) (1) NaNO2, HCl; (2) H2O D) (1) NaNO2, HCl; (2) H3PO2
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58. What starting materials are required to synthesize the following azo compound?
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Chapter 26: Carbon-Carbon Bond Forming Reactions in Organic

Synthesis
1. Organocuprate reagents (R2CuLi) react with several compounds. Which listed reaction
is not correct?
A) Acid chlorides react with organocuprate reagents to form ketones.
B) Epoxides react with organocuprate reagents to form alcohols.
C) Alkyl halides react with organocuprate reagents to form coupling products
containing a new carbon-carbon bond.
D) Carbon dioxide reacts with organocuprate reagents to form carboxylic acids.
2. Which class of compounds listed below does not react with organocuprate reagents to
form a coupling product that contains a new carbon-carbon bond?
A) 1° alkyl halides B) 3° alkyl halides C) vinyl halides D) aryl halides
3. Which statement below best explains what is meant by the statement, "An
organocuprate reaction with a vinyl halide is stereospecific"?
A) The reaction of a specific stereoisomer with the R2CuLi reagent will yield that
particular stereoisomer as the product.
B) The reaction of a vinyl halide with the R2CuLi reagent will only yield the cis
product.
C) The reaction of a vinyl halide with the R2CuLi reagent will only yield the trans
product.
D) The reaction of a vinyl halide with the R2CuLi reagent will only yield one
enantiomer product—either R or S configuration.
4. Coupling reactions with vinyl halides are stereospecific. Which choice below best
describes the expected product when trans-1-bromo-1-hexene reacts with (CH3)2CuLi?
A) The reaction will only yield a trans-alkene.
B) The reaction will only yield a cis-alkene.
C) The reaction will only yield one enantiomeric product with R configuration.
D) The reaction will only yield one enantiomeric product with S configuration.
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Page 284
8. What is the missing reactant in the following reaction?
9. Identify the products of the following reaction.
A) A B) B C) C D) D
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10. Identify the products of the following reaction.
11. Which of the reactions listed below is not stereospecific?

A) Suzuki reaction C) Heck reaction
B) organocuprate coupling reaction D) Simmons-Smith reaction
12. Choose the statement below that is not true about the Suzuki reaction.
A) The product of the Suzuki reaction is completely stereospecific.
B) The Suzuki reaction involves both an organoborane reagent and an
organopalladium catalyst.
C) The Suzuki reaction forms more highly substituted alkenes.
D) The Suzuki reaction involves an oxidative addition followed by a reductive
elimination.
13. Which of the following is not a step in the Suzuki reaction?

A) Oxidative addition of R-X to the palladium catalyst
B) Substitution of the R group to the palladium catalyst
C) Transfer of the alkyl group from the organoborane to palladium
D) Reductive elimination of R-R, forming the new C-C bond
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14. What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have
in common when they react with an alkyl halide?
A) All reactions form new carbon-carbon bonds.
B) They all use palladium as a catalyst in one step of the reaction.
C) They are all stereospecific reactions.
D) They all require harsh conditions.
15. Which of the following statements is not true about the Simmons-Smith reaction?
A) The Simmons-Smith reaction involves the formation of a free carbene.
B) The Simmons-Smith reaction uses the reagents zinc-copper couple.
C) The Simmons-Smith reaction is stereospecific.
D) The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc
reagent.
16. Which of the following is true about the use of the Grubbs catalyst?
A) The Grubbs catalyst is used in carbon-carbon coupling reactions.
B) The Grubbs catalyst is used in alkene metathesis.
C) The Grubbs catalyst is used in carbene formation.
D) The Grubbs catalyst is used with palladium as a co-catalyst.
17. What products are formed when diazomethane is heated?

A) methane gas and nitrogen gas C) methyl radical and nitrogen gas
B) propene gas and nitrogen gas D) methylene and nitrogen gas
18. Which of the following descriptions does not apply to methylene?

A) Methylene is sp2 hybridized.
B) Methylene is a neutral, reactive intermediate.
C) Methylene is a radical intermediate.
D) The formula of methylene is :CH2.
19. Which of the following statements is not true about a carbene?

A) A carbene is a neutral reactive intermediate.
B) A carbene contains a divalent carbon.
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C) A carbene is sp3 hybridized.

D) A carbene is surrounded by six electrons.
20. Which of the following correctly describes a reaction yielding a dichorocarbene?

A) The reaction of chloroform with KOC(CH3)3.
B) The reaction of chloroform with Zn(Cu).
C) The reaction of chloroform with (CH3)2CuLi.
D) The reaction of diazomethane with KOC(CH3)3.
21. Dichlorocarbene reacts with an alkene to form a cyclopropane derivative. In this

reaction the dichlorocarbene acts as a(n)
A) Lewis base.
B) electrophile.
C) nucleophile.
D) Brønsted-Lowry base.
22. Why is the Grubbs catalyst synthetically important?

A) Because it only requires dilute concentrations of the reactants.
B) Because it produces only stereospecific products.
C) Because it produces only stereoselective products.
D) Because it provides a synthetic pathway for ring-closing metathesis reactions.
23. What would be the starting material for the following product that was made via a
Grubbs catalyst?
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24. Identify the starting material that would be used to form the following product in a ring-
closing metathesis reaction utilizing a Grubbs catalyst?
25. Identify the major organic product of the following reaction.
26. What would be the major organic product of the following Heck reaction?
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29. Identify the structure of the organic product Y formed in the following reaction
sequence.
30. What is the name for the type of intermediate X formed in the reaction sequence below?
A) a carbocation B) a carbanion C) a free radical D) a carbene
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31. As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1-
dichloro-2,3-dimethylcyclopropane is formed. What can we conclude about the nature
of the reaction mechanism?
A) The mechanism is an SN1 mechanism.

B) The mechanism is a concerted.
C) The mechanism proceeds through a radical intermediate.
D) The mechanism is an E2 mechanism.
A) I B) II C) III D) None of the choices is correct
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34. Identify the structure of the organic product Y formed in the following reaction
sequence.
35. Many of the reactions studied in this chapter are stereospecific. Why are stereospecific
reactions important?
A) When a reaction produces a mixture of enantiomers, it is often very difficult to
separate them. A mixture of products is often not useful.
B) Often stereoisomers of a particular compound will have very different biological
effects on an organism. Only one isomer is biologically helpful, and the other may
be harmful.
C) Often only one stereoisomer is biologically active, and coupling reactions are often
used for the production of biological materials.
D) All of the choices are true.
36. What starting material could yield the following compound if Simmons-Smith
conditions were used?
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37. What starting material could yield the following compound if Simmons-Smith
conditions were used?
38. Identify the structure of the major organic product that results from the following
reaction.
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39. Compound X can be synthesized via a ring-closing metathesis reaction when treated
with a Grubbs' catalyst. What is a possible structure of the starting material for this
reaction?
40. What is the appropriate sequence of reagents that will produce the target molecule
shown below from ethylbenzene?
A) (1) HBr, H2O2; (2) KOC(CH3)3 ; (3) MCPBA; (4) CH2=CPh2

B) (1) NBS, h ; (2) KOC(CH3)3 ; (3) CHBr3, KO(CH3)3 ; (4) a. LiCuPh2, b. H2O
C) (1) H2SO4(aq.),  ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) CH2=CPh2
D) (1) Br2, FeBr3 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) Ph2COCl
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41. What is the appropriate sequence of starting material and reagents that will produce the
target molecule shown below?
Chapter 27: Pericyclic Reactions
1. Which of the following statements about pericyclic reactions is true?

A) Pericyclic reactions occur by way of ionic intermediates.
B) Pericyclic reactions occur by way of radical intermediates.
C) Pericyclic reactions involve multiple steps.
D) Reactive intermediates are not formed in pericyclic reactions.
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2. Which of the following statements about pericyclic reactions is true?

A) In pericyclic reactions, bonds are broken and formed in multiple steps.
B) In pericyclic reactions, all bonds are broken and formed in a single step.
C) One intermediate has been identified in pericyclic reactions.
D) The transition state in a pericyclic reaction is acyclic.
3. Which of the following statements about pericyclic reactions is not true?

A) Pericyclic reactions are concerted reactions.
B) Pericyclic reactions proceed through a cyclic transition state.
C) Pericyclic reactions are not stereospecific.
D) Pericyclic reactions require light or heat.
4. Which of the following is a type of pericyclic reaction?

A) electrocyclic reactions C) cycloelimination reactions
B) acyclic reactions D) electrophilic reactions
5. Which of the following is not a type of pericyclic reactions?

A) cycloadditions C) electrocyclic reactions
B) nucleophilic reactions D) sigmatropic rearrangements
6. Which of the following statements about electrocyclic ring closure is not true?
A) It is an intramolecular reaction.
B) It requires heat or light.
C) The cyclic product contains one more  bond and one fewer  bond than the
reactants.
D) The cyclic product contains one more  bond and one fewer  bond than the
reactants.
7. Which of the following statements about an electrocyclic ring-opening reaction is not

true?
A) An electrocyclic ring-opening reaction is an intramolecular reaction.
B) An electrocyclic ring-opening reaction requires a source of energy (heat or light).
C) The product of an electrocyclic ring-opening reaction contains one fewer  bond
than the reactant.
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D) The product of an electrocyclic ring-opening reaction contains one more  bond

than the reactant.
8. What is the organic product of the following electrocyclic reaction?
9. Which of the following statements about cycloaddition reactions is true?

A) Cycloaddition reactions occur only intermolecularly.
B) Cycloaddition reactions occur only intramolecularly.
C) Cycloaddition reactions form a cyclic product with two new  bonds.
D) Cycloaddition reactions can be intramolecular or intermolecular.
10. Which of the following statements about sigmatropic reactions is true?

A) The reactants contain one more  bond than the product.
B) The product contains one more  bond than the reactant.
C) A  bond is broken in the reactant.
D) A  bond is broken in the reactant.
A) cycloaddition reaction C) electrophilic reaction

B) electrocyclic reaction D) sigmatropic reaction
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A) cycloaddition reaction C) electrophilic reaction

B) electrocyclic reaction D) sigmatropic reaction
A) cycloaddition reaction C) electrocyclic reaction

B) electrophilic reaction D) sigmatropic reaction
A) cycloaddition reaction C) electrocyclic reaction

B) electrophilic reaction D) sigmatropic reaction
15. Which of the following statements about  orbitals is true?

A)  orbitals are formed by the linear combination of two sp3 orbitals.
B)  orbitals are formed by the linear combination of two sp2 orbitals.
C)  orbitals are formed by the linear combination of two sp orbitals.
D)  orbitals are formed by the linear combination of two p orbitals.
16. Which of the following statements about molecular orbitals is true?

A) The number of molecular orbitals formed is different from the number of atomic
orbitals used.
B) The number of molecular orbitals formed is equal to the number of atomic orbitals
used.
C) The number of molecular orbitals formed is equal to twice the number of atomic
orbitals used.
D) The number of molecular orbitals formed is equal to half the number of atomic
orbitals used.
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17. Which of the following statements about a -bonding molecular orbital is true?
A) A -bonding molecular orbital is formed when two p orbitals of similar phase
overlap.
B) A -bonding molecular orbital is lower in energy than a -bonding molecular
orbital.
C) A -bonding molecular orbital is formed when two p orbitals of opposite phase
overlap.
D) Both the statements “a -bonding molecular orbital is formed when two p orbitals
of similar phase overlap” and a -bonding molecular orbital is lower in energy than
a -bonding molecular orbital” are true.
18. Which of the following statements about a * antibonding molecular orbital is true?
A) A * antibonding molecular orbital is formed when two p orbitals of similar phase
overlap.
B) A * antibonding molecular orbital is formed when two p orbitals of opposite
phase overlap.
C) A * antibonding molecular orbital is a higher-energy molecular orbital than a 
bonding molecular orbital.
D) Both the statements “a * antibonding molecular orbital is formed when two p
orbitals of opposite phase overlap” and “a * antibonding molecular orbital is a
higher-energy molecular orbital than a  bonding molecular orbital” are true.
19. How many  molecular orbitals are present in 1,3,5-hexatriene?

A) 3 B) 4 C) 5 D) 6
20. How many bonding molecular orbitals are present in 1,3,5-hexatriene?

A) 3 B) 4 C) 5 D) 6
21. How many  molecular orbitals are present in 1,3,5,7,9-decapentaene?

A) 4 B) 5 C) 10 D) 12
22. How many bonding molecular orbitals are present in 1,3,5,7,9-decapentaene?

A) 4 B) 5 C) 10 D) 12
23. How many nodes are present in 5 of 1,3,5,7,9-decapentaene?

A) 2 B) 3 C) 4 D) 5
24. Which of the following statements about electrocyclic reactions is true?

A) An electrocyclic reaction is generally irreversible.
B) Generally, an acyclic triene is favored over a six-membered ring at equilibrium.
C) Generally, a four-membered ring is favored over an acyclic diene at equilibrium.
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D) An electrocyclic reaction is generally reversible.
25. Predict the major organic product(s) of the following electrocyclic reaction.
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29. Which of the following statements about thermal electrocyclic reactions is not true?
A) The number of  bonds in the conjugated polyene determines whether rotation is
conrotatory or disrotatory.
B) Thermal electrocyclic reactions occur in a disrotatory fashion for a conjugated
polyene with an odd number of  bonds.
C) Thermal electrocyclic reactions occur in a conrotatory fashion for a conjugated
polyene with an even number of  bonds.
D) In thermal reactions, we consider the orbitals of the HOMO of the ground state
electronic configuration to determine the course of the reaction.
30. Which of the following statements about photochemical electrocyclic reactions is not
true?
A) In photochemical reactions, we consider the orbitals of the HOMO of the excited
state to determine the course of the reaction.
B) Photochemical electrocyclic reactions occur in a conrotatory fashion for a
conjugated polyene with an odd number of  bonds.
C) Photochemical electrocyclic reactions occur in a disrotatory fashion for a
conjugated polyene with an even number of  bonds.
D) In photochemical reactions, we consider the orbitals of the LUMO of the excited
state to determine the course of the reaction.
31. Which of the following statements about cycloaddition reactions is not true?
A) Cycloaddition reactions form a cyclic product with two new  bonds.
B) The course of the reaction is determined by the symmetry of the molecular orbitals
of the products.
C) Cycloaddition reactions are concerted.
D) Cycloaddition reactions are stereospecific.
32. Which of the following statements about cycloaddition reactions is true?

A) Cycloaddition reactions can be initiated by heat only.
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B) Cycloaddition reactions can be initiated by light only.

C) Cycloaddition reactions can be initiated by heat or light.
D) Cycloaddition reactions are identified by the number of  electrons in the two
products.
33. Why is the Diels-Alder reaction called a thermal [4+2] cycloaddition?

A) Because the reaction is initiated by heat; the diene has four  electrons and the
dienophile has two  electrons.
B) Because the reaction is initiated by light; the diene has four  electrons and the
dienophile has two  electrons.
C) Because the reaction is initiated by heat; the dienophile has four  electrons and the
diene has two  electrons.
D) Because the reaction is initiated by light; the dienophile has four  electrons and
the diene has two  electrons.
34. Which of the following statements about [2+2] cycloaddition reactions between two
alkenes is true?
A) The reaction is initiated by heat.
B) The reaction is initiated by light.
C) The product is a cyclopentane derivative.
D) Each reactant contains two  electrons that participate in the formation of new
bonds.
35. What type of cycloaddition reaction is shown below?
A) [2+2] B) [4+2] C) [4+4] D) [0+2]
36. What type of cycloaddition reaction is shown in the following equation?
A) [2+2] B) [4+2] C) [4+4] D) [0+2]
37. What are the two modes of bond formation in cycloaddition reactions?
A) suprafacial and antarafacial bond formations.
B) superfacial and antifacial bond formations.
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C) suprafacial and synfacial bond formations.

D) synfacial and antifacial bond formations.
38. Which of the following statements about orbital symmetry and cycloaddition reactions
is true?
A) Thermal cycloadditions involving an even number of  bonds proceed by a
suprafacial pathway.
B) Thermal cycloadditions involving an odd number of  bonds proceed by a
C) Photochemical cycloadditions involving an odd number of  bonds proceed by a
D) Photochemical sycloadditions involving an even number of  bonds proceed by an
antarafacial pathway.
39. Which of the following statements about orbital symmetry and cycloaddition reactions
is true?
A) Thermal cycloadditions involving an even number of  bonds proceed by a
B) Thermal cycloaddition involving an odd number of  bonds proceed by an
C) Photochemical cycloadditions involving an even number of  bonds proceed by an
D) Photochemical cycloadditions involving an even number of  bonds proceed by a
40. Which of the following statements about sigmatropic reactions is not true?
A) A sigmatropic reaction is an intramolecular pericyclic reaction.
B) In a sigmatropic reaction,  bond is broken in one of the reactants.
C) The  bonds rearrange in a sigmatropic reaction.
D) The number of  bonds in the reactants and product differs in a sigmatropic
reaction.
41. Which of the following is not a correct designation for a sigmatropic rearrangement?
A) [1,3] B) [1,5] C) [3,3] D) [3,1]
42. What type of sigmatropic rearrangement is illustrated below?
A) [1,3] B) [1,4] C) [3,3] D) [1,5]
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A) [1,3] B) [1,4] C) [3,3] D) [1,5]
A) [1,3] B) [1,4] C) [3,3] D) [1,5]
45. Which of the following statements about sigmatropic rearrangements and orbital
symmetry is not true?
A) Reactions involving six atoms or fewer must take place by suprafacial pathways.
B) In a suprafacial rearrangement, the new  bond forms on the opposite side of the 
system as the broken  bond.
C) In an antarafacial rearrangement, the new  bond forms on the opposite side of the
 system as the broken  bond.
D) In a suprafacial rearrangement, the new  bond forms on the same side of the 
system as the broken  bond.
46. Which of the following statements about the Cope rearrangement is not true?
A) The Cope rearrangement involves the rearrangement of a 1,5-diene to an isomeric
1,5-diene.
B) The Cope rearrangement takes place readily in a suprafacial pathway under
photochemical conditions.
C) The Cope rearrangement involves three electron pairs; two in  bonds and one in a
 bond.
D) The Cope rearrangement takes place readily in a suprafacial pathway, when heated.
47. Which of the following statements about the Claisen rearrangement is true?
A) The Claisen rearrangement occurs readily in a suprafacial pathway under
photochemical conditions.
B) The Claisen rearrangement occurs readily in an antarafacial pathway under thermal
conditions.
C) The Claisen rearrangement involves three electron pairs; two in  bonds and one in
a  bond.
D) The Claisen rearrangement involves the rearrangement of an unsaturated ether to a
,-unsaturated carbonyl compound.
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48. What is the major organic product of the following Cope rearrangement?
49. What is the major organic product of the following oxy-Cope rearrangement?
50. What is the major organic product of the following Claisen rearrangement?
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51. What is the major organic product of the following Claisen rearrangement?
52. Which of the following statements about a thermal reaction involving an even number
of electron pairs is true?
A) A thermal reaction involving an even number of electron pairs is conrotatory or
antarafacial
B) A thermal reaction involving an even number of electron pairs is disrotatory or
suprafacial
C) A thermal reaction involving an even number of electron pairs is conrotatory or
suprafacial
D) A thermal reaction involving an even number of electron pairs is disrotatory or
antarafacial
Chapter 28: Carbohydrates
1. Which of the following compounds is an aldose?
A) A B) B C) C D) D
2. How many carbons does a pentose sugar have?

A) 2 B) 3 C) 4 D) 5
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3. How many possible stereoisomers are there of the following heptose?
A) 16 B) 21 C) 32 D) 64
4. Is the following carbohydrate D or L? Provide an explanation for your answer.
A) It is D because the OH group on C2 is on the right.

B) It is L because the OH group on C4 is on the left.
C) It is L because the OH group on C3 is on the left.
D) It is D because the sugar is not symmetric.
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5. Which of the following compounds is a  anomer?
A) A B) B C) C D) D
6. Which is the correct Haworth projection for the  anomer of allose?
A) A B) B C) C D) D
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7. Which is the correct Haworth projection for the  anomer of D-glucose?
A) A B) B C) C D) D
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8. Which is the correct Fischer projection for the open-chain form of the carbohydrate
shown below?
A) A B) B C) C D) D
9. Does a monosaccharide prefer to exist in the open-chain or closed-ring form?

A) open B) closed C) Both forms exist in equal ratios.
10. What is the process called for the interconversion of one anomer to the other?
A) racemization B) mutarotation C) epimerization D) enolization
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11. What is the correct chair form for the  anomer of D-mannose?
A) A B) B C) C D) D
12. What is the correct chair form for the  anomer of D-glucose?
A) A B) B C) C D) D
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13. Which of the following reagents would convert glucose into ethyl glucopyranoside?
A) EtBr, aq. HCl
B) EtOH, aq. HCl
C) EtOH, NaOH
D) Ag2O in NH4OH
14. Which of the following is a reducing sugar?
A) A B) B C) C D) D
15. Which of the following reagents will selectively oxidize an aldose to an aldonic acid?
A) PCC B) Ag2O in NH4OH C) FeCl3 D) HNO3
16. Which of the following pairs of carbohydrates will afford the same product from a Wohl
degradation?
A) xylose/glucose
B) ribose/arabinose
C) fructose/mannose
D) lyxose/threose
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17. What are the products of the following reaction?
A) A B) B C) C D) D
18. Which of the following compounds is not a valid representation for D-glucose?
A) A B) B C) C D) D E) E
19. Cellulose is a polysaccharide with ________________________ linkages.

A) -1,4'-glycosidic C) -1,6'-glycosidic
B) -1,4'-glycosidic D) -1,6'-glycosidic
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20. Amylose is a polysaccharide with ________________________ linkages.

A) -1,4'-glycosidic C) -1,6'-glycosidic
B) -1,4'-glycosidic D) -1,6'-glycosidic
21. The branching units in amylopectin, a polysaccharide, which enable this molecule to be
water soluble are connected with __________________________ linkages.
A) -1,4'-glycosidic C) -1,6'-glycosidic
B) -1,4'-glycosidic D) -1,6'-glycosidic
22. What is the composition of lactose?

A) two glucose units with a -1,4'-glycoside bond
B) one glucose and one fructose unit with a -glycosidic bond to the 2'carbon of a
fructofuranose ring
C) one galactose and one glucose unit with a -1,4'-glycoside bond
D) repeating unit of glucose units joined in a -1,4'-glycosidic linkage
23. What is the composition of sucrose?

fructofuranose ring
24. What is the composition of maltose?

fructofuranose ring
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25. From the sugars shown below, which one is a non-reducing sugar?
A) A B) B C) C D) D
26. From the disaccharides listed below, which one will not undergo mutarotation?
A) sucrose B) maltose C) lactose D) xylobiose
27. Upon hydrolysis of cellulose, what sugar is formed?

A) sucrose B) maltose C) lactose D) glucose
28. Upon hydrolysis of amylose, what sugar is formed?

29. Upon hydrolysis of amylopectin, what sugar is formed?

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30. From the sugars shown below, which one will not give a positive test with Tollens
reagent?
A) A B) B C) C D) D
31. What is the best description of the product formed in the following reaction sequence?
A) The product is an optically active aldonic acid.

B) The product is an optically inactive aldonic acid.
C) The product is an optically active aldaric acid.
D) The product is an optically inactive aldaric acid.
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32. The following reaction is an example of a base-catalyzed epimerization reaction in

which a ketose is converted to a pair of aldoses. What are the products from this
reaction?
A) D-glucose and D-mannose C) D-talose and D-idose

B) D-galactose and D-talose D) D-glucose and D-idose
33. Which sugar is represented by the line angle structure below?
A) D-fructose B) D-sorbose C) L-psicose D) L-tagatose
34. Oxidation of a D-hexose with nitric acid forms an optically active aldaric acid. A Wohl
degradation of the same D-hexose followed by oxidation with nitric acid forms an
optically active aldaric acid. What are the three possible D-hexoses that fit this data?
A) D-allose, D-altrose and D-glucose C) D-glucose, D-idose and D-altrose
B) D-glucose, D- mannose and D-talose D) D-galactose, D-talose and D-mannose
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35. After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was

isolated from the reaction mixture. The following experimental data was obtained.
What is the structure of this unknown sugar?
Data:
- Molecular formula: C6H12O6
- Reacts with phenylhydrazine to give an osazone, mp 178°C.
- Reacts with HNO3 to give an optically active aldaric acid.
- Wohl degradation followed by HNO3 oxidation gives an optically inactive
aldaric acid.
- Two Wohl degradations followed by HNO3 oxidation give a meso-tartaric acid.
A) A B) B C) C D) D
36. Which of the following sugars can be classified as an aldohexose?
A) A B) B C) C D) D
37. Which of the following sugars can be classified as a ketohexose?
A) A B) B C) C D) D
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38. Which of the following sugars can be classified as a ketotetrose?
A) A B) B C) C D) D
39. Which of the following sugars can be classified as a ketopentose?
A) A B) B C) C D) D
40. Which of the following best describes the relationship between D-glucose and D-
fructose?
A) enantiomers B) epimers C) anomers D) constitutional isomers
41. What is the classification of pyranose forms of monosaccharides?

A) 5-membered cyclic hemiacetals C) 5-membered cyclic acetals
B) 6-membered cyclic acetals D) 6-membered cyclic hemiacetals
Chapter 29: Amino Acids and Proteins
Page 319
1. Which of the following compounds is not an amino acid?
A) A B) B C) C D) D
2. What is the configuration of naturally occurring amino acids?

A) D B) S C) L D) R
3. Which is the correct structure for serine?
A) A B) B C) C D) D
4. Which is the correct structure for the amino acid proline?
A) A B) B C) C D) D
5. Which is the correct structure for the amino acid cysteine?
A) A B) B C) C D) D
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6. Which is the correct structure for the amino acid valine?
A) A B) B C) C D) D
7. Which of the following is the correct structure for alanine at pH = 7?
A) A B) B C) C D) D
8. Which of the following is the correct structure for aspartic acid at pH = 1?
A) A B) B C) C D) D
9. Which of the following aldehydes would be a good starting material in the Strecker
synthesis of phenylalanine?
A) A B) B C) C D) D
10. What reagents would you use to convert acetaldehyde into alanine?
A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2
11. What is the separation of a racemic mixture into its component enantiomers called?
A) diastereomers B) meso C) resolution D) neutralization
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12. Why does the formation of salts of a racemic mixture of N-acetyl valine with a single
enantiomer of -methylbenzylamine enable the separation of the two enantiomers of N-
acetyl valine?
A) They form amides. C) They form salts.
B) They form diastereomers. D) They form meso compounds.
13. Why can glycine not be resolved into two enantiomers?

A) It has no stereogenic centers. C) It has no aromatic rings.
B) It has no nitrogen atoms. D) It cannot be converted into a salt.
14. What amino acid is at the N-terminus of the following peptide?
A) valine B) serine C) alanine D) proline
15. What amino acid is at the C-terminus of the following peptide?
A) valine B) serine C) alanine D) proline
16. Why is the s-trans form of an amide bond more stable?

A) There is no s-cis form in an amide bond.
B) The oxygen is hydrogen-bonded with the nitrogen atom.
C) The nitrogen is able to be sp2-hybridized.
D) The more sterically bulky groups are farther apart.
17. Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room
temperature?
A) These amide bonds are not stable.
B) There is partial double bond character between the carbonyl carbon and the
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nitrogen atom.
C) The oxygen atom is hydrogen-bonded with the nitrogen atom.
D) The side-chains can form hydrogen bonds.
18. Which of the following is the major advantage of the Merrifield synthesis of peptides?
A) It allows for the formation of absolutely no by-products.
B) Impurities can be easily washed away.
C) Excess reagent can be used.
D) It prevents hydrogenation.
19. What are the basic steps in the Merrifield peptide synthesis?
A) coupling and hydrolysis C) deprotection and hydrogenation
B) hydrolysis and deprotection D) coupling and deprotection
20. Which of the following is the structure of the amino acid lysine?
A) A B) B C) C D) D
21. What is (are) the missing reagent(s) in the reaction below?
A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2
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22. What is the major organic product for the following reaction?
A) A B) B C) C D) D
23. What is the IUPAC or common name for the following compound?
A) cysteinylalanine B) alanylcysteine C) serinylalanine D) alanylserine
24. Amino acid synthesis is possible by all except one of the pathways listed. Which is not a
synthetic pathway for amino acids?
A) Amination of malonic ester followed by hydrolysis and decarboxylation.
B) Nucleophilic addition of NH3 to an aldehyde followed by addition of cyanide to the
imine, and, finally, hydrolysis.
C) SN2 reaction using an -halo carboxylic acid with ammonia as the nucleophile.
D) Reaction of NH4Cl and NaCN with an aldehyde followed by an acidic work-up.
25. Which of the following correctly describes a protein?

A) a dipeptide; two amino acids joined together by one amide bond
B) a tripeptide; three amino acids joined together by two amide bonds
C) a polymer of more than 40 amino acids joined together by amide bonds
D) a polypeptide of any number of amino acids joined together by amide bonds
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26. Which of the following correctly describes a peptide bond?

A) a bond between sp3-hybridized atoms only
B) a bond usually found in the s-cis conformation
C) an amide bond
D) the result of the formation of the carbonyl group of one amino acid with a R-group
from the other amino acid
27. Which of the following correctly describes the Merrifield synthesis?

A) It uses a solid phase technique for the synthesis of peptides.
B) It uses DCC (dicyclohexylcarbodiimide) to form the amide bond in a peptide
synthesis.
C) It uses BOC (tert-butoxycarbonyl) as a protecting group for peptide synthesis.
D) It uses aqueous phase techniques for the synthesis of large polypeptides.
28. Which of the following correctly describes the tertiary structure of a peptide?
A) the three-dimensional conformations of localized regions of a protein
B) the particular sequence of amino acids that are joined together by peptide bonds
C) the structure is defined by the -pleated sheet form
D) the three-dimensional shape adopted by the entire peptide
29. What are the only non-covalent bonds that stabilize the tertiary structure of a peptide?
A) hydrogen bonds
B) disulfide bonds
C) Van der Waal bonds
D) ionic bonds
30. Which of the following is (are) globular protein(s)?

A) hemoglobin B) keratins C) collagens D) elastins
31. Which of the following is (are) fibrous protein(s)?

A) keratins B) hormones C) enzymes D) antibodies
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32. What is the appropriate sequence of reaction conditions used to synthesize valine from
acetamidomalonic ester?
A) (1) NaOH; (2) (CH3)2CHBr; (3) Cl2, H2O, heat

B) (1) NaOCH2CH3; (2) (CH3)2CH2CHBr; (3) HCl, H2O, heat
C) (1) NaOCH2CH3; (2) (CH3)2CHBr; (3) HCl, H2O, heat
D) (1) NaOH; (2) CH3CH2CH2Br; (3) HCl, H2O, heat
33. Below is a 2D chromatogram that shows the separation of five amino acids. In this
technique, the amino acid mixture is first separated by chromatography using a polar
solvent system. Then the plate is rotated 90°, and the amino acids are further separated
by electrophoresis. Identify the spots obtained from a mixture of Trp, Glu, Lys, Ile and
Thr. A table with isoelectric points is included to aid in solving this problem.
amino acid pI value

Trp 5.9
Glu 3.2
Lys 9.7
Ile 6.0
Thr 5.6
A) 1=Lys, 2=Thr, 3=Glu, 4=Trp, 5=Ile C) 1=Lys, 2=Ile, 3=Glu, 4=Trp, 5=Thr
B) 1=Glu, 2=Thr, 3=Lys, 4=Trp, 5=Ile D) 1=Glu, 2=Ile, 3=Lys, 4=Trp, 5=Thr
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34. Below is a proposed method for resolving a racemic mixture of (R)- and (S)-
phenylalanine. Upon separation of the products, will this method produce (R)- or (S)-
phenylalanine?
A) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-

amino acids.
B) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-
amino acids.
C) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-
amino acids.
D) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-
amino acids.
35. Give the order (1st to last) in which the following amino acids would be eluted with a
buffer of pH = 4 from a column containing a cationic-exchange resin (Dowex 50): Arg
(pI = 10.8), Ser (pI = 5.7), Asp (pI = 2.8) and His (pI = 7.6).
A) His, Ser, Asp, Arg C) His, Ser, Arg, Asp
B) Arg, His, Ser, Asp D) Asp, Ser, His, Arg
36. Reaction of a polypeptide, composed of 12 amino acids, with carboxypeptidase A

releases Met (C-terminal amino acid). The polypeptide undergoes partial hydrolysis to
give 12 groups of peptides. Use the groups of overlapping amino acids to determine the
proper sequence of this polypeptide. Note: Since these lists of peptides are separated by
commas, they are not necessarily in the proper sequence.
1. Ser, Lys, Trp 5. Met, Ala, Gly 9. Lys, Ser

2. Gly, His, Ala 6. Ser, Lys, Val 10. Glu, His, Val
3. Glu, Val, Ser 7. Glu, His 11. Trp, Leu, Glu
4. Leu, Glu, Ser 8. Leu, Lys, Trp 12. Ala, Met
A) Met-Ala-Gly-His-Glu-Val-Ser-Lys-Trp-Leu-Glu-Ser
B) Met-Ala-Gly-Glu-His-Ser-Val-Lys-Trp-Leu-Glu-Ser
C) Ser-Glu-Leu-Trp-Lys-Ser-Val-Glu-His-Gly-Ala-Met
D) Ser-Lys-Leu-Trp-Lys-Ser-Val-His-Glu-Gly-Ala-Met
37. What is formed by the combination of four amino acids?

A) a protein B) a polypeptide C) a tripeptide D) a tetrapeptide
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38. Which of the following amino acids is achiral?

A) phenylalanine B) glycine C) valine D) alanine
39. Which of the following amino acids does not have an L-isomer?
A) alanine B) valine C) glycine D) leucine
40. Which one of the following naturally occurring amino acids does not have an S
configuration?
A) cysteine B) alanine C) tyrosine D) isoleucine
41. What is the name given to the pH at which the concentration of the zwitterionic form of
an amino acid is at a maximum concentration?
A) electric point B) dipolar point C) neutral point D) isoelectric point
Chapter 30: Lipids
1. Provide a definition of the term lipid.

A) a compound with a carbonyl group C) a hydrophobic biomolecule
B) a compound with an aromatic ring D) a water-soluble compound
2. Which of the following compounds is not a lipid?
A) A B) B C) C D) D
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3. Which of the following compounds is not a hydrolyzable lipid?
A) A B) B C) C D) D
4. Evaluate the following statement: The terpene structure shown is a hydrolysable lipid.
A) True, because it contains an alcohol functional group.

B) False, because alcohol and aldehyde moieties are not hydrolysable.
C) True, because there are three polar groups and only 12 total carbon atoms.
D) False, because there is too much steric repulsion from the alcohol and aldehyde
moieties.
5. What happens to the melting point in fatty acids as the unsaturation increases?
A) It increases
B) It decreases.
C) There is no direct correlation between unsaturation and melting point.
D) The melting point stays the same.
6. Solid fats are generally from what source?

A) vegetables B) starches C) legumes D) animals
7. Liquid oils usually have a higher percentage of what component compared to solid fats?
A) oxygen B) hydrogen C) unsaturation D) aromatic rings
8. How can an unsaturated fatty acid be converted into a saturated fatty acid?
A) hydrogenation B) hydration C) ozonolysis D) hydrolysis
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9. What chemical process causes an oil (such as soybean oil) to become rancid?
A) hydrogenation with hydrogen C) oxidation with molecular oxygen
B) hydration with water D) bromination with bromine
10. What is the main cellular function of a triacylglycerol?

A) signal transduction C) nerve cell transferal
B) form cell membranes D) energy storage
11. Which of the following is a phospholipid?
A) A B) B C) C D) D
12. What is the purpose of vitamin K?

A) energy storage B) blood clotting C) photosynthesis D) hydrogenation
13. Eicosanoids are derived from what compound?

A) arachidonic acid B) cyclohexane C) cholesterol D) triacyl glycerols
14. What is the first key enzyme required for the synthesis of prostaglandins from
arachidonic acid?
A) protein Kinase C
B) synthase
C) transferase
D) COX (cyclic oxygenase)
15. What is (are) the basic subunits of terpenes?

A) cyclohexane B) triacyl glycerols C) isoprene D) carbonyls
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16. How many isoprene units are in the following molecule?
A) 1 B) 2 C) 3 D) 4
17. How many isoprene units are contained in the following molecule?
A) 5 B) 4 C) 3 D) 2
18. Which of the following compounds is a steroid?
A) A B) B C) C D) D
19. What is (are) the biological precursor(s) for the formation of the steroid skeleton found
in cholesterol?
A) cyclohexane B) squalene C) triacyl glycerols D) arachadonic acid
20. Which structure represents the lowest energy conformation of a trans-decalin?
A) A B) B C) C D) D
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21. Which of the following sequences shows a reasonable series of 1,2-rearrangements as

might be found in the biosynthesis of a steroid?
A) A B) B C) C D) D
22. Which of the following is not one of the three main categories of hydrolyzable lipids?
A) waxes B) steroids C) triacylglycerols D) phospholipids
23. Which of the following classes of molecules is not a nonhydrolyzable lipid?

A) steroids B) terpenes C) phospholipids D) eicosanoids
24. All except one of the statements below are true about the molecule given. Which
statement is not correct?
A) This molecule is a phospholipid and is generally found in fruits, vegetables, fish,

liver, and dairy products.
B) This molecule is a phospholipid that composes the main fabric of the insoluble
barrier that protects the cell.
C) This molecule contains two fatty acids and has at least one stereogenic center.
D) This molecule is a phospholipid and belongs to the general category of lecithins.
25. From the statements below, pick out the one that is not correct for fat-soluble vitamins.
A) Fat-soluble vitamins are classified as lipids.
B) Fat-soluble vitamins are a group of biologically active compounds containing 20
carbon atoms.
C) Fat-soluble vitamins are required in small quantities for normal metabolism.
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D) Fat-soluble vitamins are stored in fat cells for use when they are needed.
26. What is the result of the oxidation of arachidonic acid with O2 by cyclooxygenase?
A) It results in the synthesis of prostaglandins, thromboxanes, and prostacyclins.
B) It results in the synthesis of fat-soluble vitamins from sphingomyelins.
C) It results in the synthesis of phosphoacylglycerols.
D) It is an important step in the synthesis of lipids that form the lipid bilayer.
27. Triacylglycerol A yields compound B when treated with excess H2, Pd-C. Ozonolysis
of A affords three molecules of compound C and one molecule of compound D. What is
the structure of A?
Choices for Triglycerol A:
A) A B) B C) C D) D
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28. Patchouli alcohol is an example of a terpene. How is this molecule classified?
A) monoterpene B) diterpene C) triterpene D) sesquiterpene
29. The stereoselective introduction of the C15 OH group on the  side chain of
prostaglandins has presented a challenge for synthetic chemists. Recently, Mulzer and
co-workers demonstrated a new route in which the  side chain is synthesized
independently and then attached to the bicyclic counterpart. What is the appropriate
sequence of reagents for the following synthesis?
A) (1) PBr3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3

B) (1) PCC; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X
C) (1) PBr3; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X
D) (1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3
Page 334
30. Norethindrone is a synthetic steroid that is better than progesterone in suppressing

ovulation. What reagents (1-3) are required to convert norethindrone to the derivatives
shown below?
A) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. O3, b. Zn, DMS
B) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, mild acid; (3) a. O3, b. Zn, DMS
C) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. OsO4, b. NaHSO3
D) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, mild acid; (3) a. OsO4, b. NaHSO3
31. Sphingomyelins are a major component of the myelin sheath. Damage to the myelin
sheath results in such diseases as multiple sclerosis. Which compound below
corresponds to a sphingomyelin?
A) A B) B C) C D) D
32. Which of the following are complex lipids?

A) steroids B) terpenes C) waxes D) protaglandins
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33. Which of the following are simple lipids?

A) steroids B) terpenes C) waxes D) prostaglandins
34. Which of the following correctly describes waxes?

A) long chain alcohols C) long chain ethers
B) long chain esters D) long chain fatty acids
35. What is the correct classification of the following compound?
CH3(CH2)15COOH
A) saturated triglyceride B) simple lipid C) wax D) saturated fatty acid
36. Which of the following fatty acids has the highest melting point?
A) palmitic acid B) arachidic acid C) stearic acid D) lauric acid
37. Which of the following fatty acids has the lowest melting point?
A) palmitic acid B) arachidic acid C) stearic acid D) lauric acid
38. Which of the following fatty acids has the highest melting point?
A) linoleic acid B) oleic acid C) arachidonic acid D) palmitoleic acid
39. Which of the following fatty acids has the lowest melting point?
A) linoleic acid B) oleic acid C) arachidonic acid D) palmitoleic acid
40. Which of the following fatty acids is not present in natural fats and oils?
A) hexadecanoic acid C) octadecanoic acid
B) heptadecanoic acid D) none of the choices
41. What is the name of the reaction of triglycerides with a base?

A) esterification B) transesterification C) ozonolysis D) saponification
Chapter 31: Synthetic Polymers
Page 336
1. Which of the following monomers yields the polymer shown below?
A) A B) B C) C D) D
2. Which of the following is the repeating unit in polyvinyl chloride (PVC)?
A) A B) B C) C D) D
3. Which of the following is (are) addition polymer(s)?

I. polypropylene
II. Teflon
III. nylon
A) Only I B) Only II C) Only III D) Both I and II
4. Which of the following is (are) condensation polymer(s)?

I. polypropylene
II. Teflon
III. nylon
A) Only I B) Only II C) Only III D) Both II and III
5. Which one of the following monomers undergoes cationic polymerization most readily?
A) H2C=CH2 B) H2C=CHCH3 C) H2C=C(CH3)2 D) H2C=CHCN
6. Which one of the following monomers undergoes anionic polymerization most readily?
A) H2C=CH2 B) H2C=CHCH3 C) H2C=C(CH3)2 D) H2C=CHCN
7. In which type of polymer are the chains packed less tightly together, resulting in lower
melting points and a softer texture?
A) isotactic polymers C) atactic polymers
B) syndiotactic polymers D) cross-linked polymers
Page 337
8. Which of the following best describes the polymer chain shown below?
A) atactic polypropylene C) syndiotactic polypropylene

B) isotactic polypropylene D) cross-linked polypropylene
9. Which of the following is used to make Teflon?

A) fluoroethene C) 1,2-difluoroethene
B) 1,1,4,4-tetrafluorobutadiene D) tetrafluoroethylene
10. Which of the following best describes the polymer chain shown below?
A) atactic polypropylene C) syndiotactic polypropylene

B) isotactic polypropylene D) cross-linked polypropylene
11. The monomer used to make superglue is shown below. Which of the following methods
of polymerization is most suitable for this type of monomer?
A) free-radical chain-growth C) anionic chain-growth

B) cationic chain-growth D) acid-catalyzed step-growth
12. Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an
initiator?
A) free-radical chain-growth C) anionic chain-growth
B) cationic chain-growth D) acid-catalyzed step-growth
Page 338
13. Which of the following is the monomer that gives the polymer shown below?
A) A B) B C) C D) D
14. What modification occurs when a small amount of p-divinylbenzene is added to the
polymerization reaction of styrene to form polystyrene? (Recall that the vinyl group is
—CH=CH2.)
A) Cross-linking of the polystyrene
B) Isotactic stereochemistry of the polystyrene
C) Syndiotactic stereochemistry of the polystyrene
D) "Softening" of the polystyrene by a plasticizer
15. Identify the repeating unit in the polymer formed from the following reaction sequence.
A) A B) B C) C D) D
16. The acid-catalyzed dimerization of isobutylene gives a mixture of two isomeric alkenes,
A and B. Hydrogenation of this mixture gives a single C8H18 hydrocarbon. What is the
structure of this hydrocarbon?
A) 2,2,4-trimethylpentane C) 2,4-dimethylhexane
B) 2,3,4-trimethylpentane D) 2,5-dimethyhexane
Page 339
17. The repeating unit of poly(methyl methacrylate) is shown below. Which one of the
following is the monomer used to make poly(methyl methacrylate)?
A) A B) B C) C D) D
18. Which of the following monomers is used to make the polymer carbowax, shown
below?
A) A B) B C) C D) D
19. Which of the following initiators can be used for anionic chain-growth polymerization?
A) benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
D) Al(CH2CH3)3, TiCl4
20. Which of the following initiators can be used for free radical chain-growth
polymerization?
A) benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
21. Which of the following initiators is used to make isotactic polypropylene?

A) benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
Page 340
22. The repeating unit of a polymer is shown below. This polymer is formed by
A) addition of ethylene. C) 1,2 addition of butadiene.

B) addition of trans-2-butene. D) 1,4 addition of butadiene.
23. Vulcanization is the process of cross-linking polymer chains in rubber using what
chemical?
A) sulfur B) formaldehyde C) benzoyl peroxide D) ethylene glycol
24. What monomer(s) would be used to make the polyester shown below?
A) butanedioic acid C) 4-hydroxybutanoic acid

B) 4-hydroxybutanal D) butanedioic acid and 1,4-butanediol
25. Which of the following is the repeating unit of the polymer formed in the
polymerization of p-hydroxybenzoic acid?
A) A B) B C) C D) D
26. Identify the monomer(s) needed to make the following polyester.
A) 3-hydroxybutanoic acid C) butanedioic acid and ethylene glycol

B) butanedioic acid D) butanedioic acid and ethanol
Page 341
27. Which of the following is (are) repeating unit(s) of step-growth polymers?
28. Bakelite is formed by the acid-catalyzed polymerization of phenol with formaldehyde.

What is (are) the product(s) of the first step in this polymerization, shown below? (Note:
in the answers below the hydroxymethyl group is -CH2OH.)
A) ortho and para-hydroxybenzaldehyde

B) meta-hydroxybenzaldehyde
C) ortho and para-(hydroxymethyl)phenol
D) meta-(hydroxymethyl)phenol
29. What is the purpose of plasticizers?

A) to harden plastics C) to initiate polymerizations
B) to soften plastics D) to cross-link polymer chains
30. Which of the following is the repeating unit of the polymer formed in the
polymerization reaction shown below?
A) A B) B C) C D) D
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31. What is the name given to polymers that soften when heated and harden when cooled?
A) cross-linked polymers C) thermosetting polymers
B) copolymers D) thermoplastics
32. What is the structure of the polymer which results when styrene is reacted with BF3 and
H2O?
A) A B) B C) C D) D
33. Rank the following monomers (X, Y and Z) in order of increasing ability to undergo
anionic polymerization, starting with the least reactive monomer.
A) Y < X < Z B) Z < Y < X C) X < Y < Z D) Y < Z < X
Page 343
34. Melamine and formaldehyde combine to form the polymer, Melmac®. How is Melmac®
classified, and what physical characteristics are consistent with its structure?
A) polycarbonate, transparent
B) polyurethane, elastic
C) thermosetting, rigid
D) thermoplastic, can be melted and molded into new shapes
35. Which monomer and which type of initiator would you use to synthesize the following
polymer?
A) A B) B C) C D) D E) E
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36. Which of the following sets of products results if nylon 66 is treated with sulfuric acid?
A) A B) B C) C D) D
37. What is the classification of the following polymer in which X and Y represent
repeating units?
A) block copolymer C) alternating copolymer

B) homopolymer D) random copolymer
repeating units?

Page 345
repeating units?

40. What is the name given to polymers with single monomers?

A) homopolymers
B) copolymers
C) block polymers
D) random polymers
41. What is the name given to polymers with two or more different monomers?
A) homopolymers
B) copolymers
C) block polymers
D) random polymers
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Test Bank of Organic Chemistry 4th

Edition By Janice Smith

For Order This And Any Other Course, Assignments,

Chapter 1: Structure and Bonding

1. What is the ground-state electronic configuration of a carbon atom?

2. What is the ground-state electronic configuration of a fluorine atom?

3. What is the ground-state electronic configuration of a magnesium cation (Mg2+)?

4. What is the ground-state electronic configuration of a chlorine anion (Cl—)?

5. Which of the following statements about valence electrons is true?

C) They are the outermost electrons.

6. Which of the following statements about bonding is true?

7. Which of the following would you expect to have ionic bonds?

8. Which of the following molecules has nonpolar covalent bonds?

A) I, II B) I, IV C) II, III D) II, IV

A) I > II > III > IV C) IV > III > II > I

13. Which of the following Lewis structures is correct?

14. Which of the following Lewis structures is correct?

A) I, II B) I, III C) II, III D) III, IV

A) I B) II C) III D) None of the above

A) I B) II C) III D) None of the above

19. Which of the following statements about constitutional isomers is true?

25. Which of the following molecules are constitutional isomers?

A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III

27. Which of the following statements about resonance structures is true?

30. What 2 things will change between two resonance structures?

31. Which of the following is a resonance structure of the compound below?

35. Which is more important in each pair of contributing resonance structures?

A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V

37. What is the approximate C-C-C bond angle in propene, CH3CH=CH2?

38. What is the approximate H-C-O bond angle in formaldehyde, H2CO?

A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral

42. Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a

44. What is the condensed formula of the compound below?

45. Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a

46. Convert the following skeletal structure to a condensed structure.

47. Avobenzone is an active ingredient in some common sunscreens. Which of the

A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3

48. In which structure is the hybridization incorrect?

A) I = sp2; II = sp2; III = sp2. C) I = sp; II = sp2; III = sp3.

B) I = sp2; II = sp3; III = sp3. D) I = sp2; II = sp2; III = sp3.

A) I < II < III < IV C) III < II < IV < I

A) I > IV > II > III C) III > IV > II > I

63. Which compound contains the most polar bond?

64. Which of the following compounds are non-polar?

A) I, IV B) I, II C) II, III D) II, IV

65. Which of the following molecules has non-polar covalent bonds?

66. Which of the following molecules has polar covalent bonds?

Chapter 2: Acids and Bases

1. Which of the following statements is a correct definition for a Brønsted-Lowry acid?

2. Which of the following statements about a Brønsted-Lowry base is true?

3. Which of the following compounds is both a Brønsted-Lowry acid and base?

5. Which of the following species is not a Brønsted-Lowry base?

7. Which of the following species is the conjugate base of methanol, CH3OH?

9. Which of the following species is the conjugate acid of ammonia, NH3?

10. Which is the conjugate acid in the following reaction?

11. Which is the conjugate base in the following reaction?

12. Which is the conjugate acid in the following reaction?

13. Which is the conjugate base in the following reaction?

14. Which of the following statements about acid strength is true?

15. Which of the following compounds is the strongest acid?

16. Which of the following compounds is the strongest acid?

17. Which of the following compounds is the weakest acid?

18. Which of the following compounds is the weakest acid?

19. Which of the following species is the strongest base?