Version 1

Name: Class: Date:
Answer the following, in preparation for your exam. Place in LONG bond paper, compile is LONG white folder using a green fastener placed left side.
1 6 11 16 21
1. Consider the following energy diagram for an enzyme-catalyzed reaction.
2 7 12 17 22
3 8 13 18 23
4 9 14 19 24
5 10 15 20 25
26 32
Which step has the least energetic transition state?

27
a. A - C b. C - E
c. E - G d. G - I
28
2. Which of the following will not undergo catalytic reduction in the presence of H2 and metal catalyst?
29 a. b.
30
***ITEMS 31, 33-50 should be answered on the sheet itself. c. d.
Deadline 9/25/2019 on or before 3pm. Late submissions will incur deduction of 15 points. Page 1
Indicate the answer choice that best completes the statement or answers the question.
Name: Class: Date:
3. Consider the following intermediate. 8. Which of the following could act as an electrophile?
a. CN– b. NH2–
c. NH3 d. H3O+
Which is applicable to this structure?

a. results in a product which has anti stereochemistry b. produces only the cis isomer
c. is called a bromohydrin d. occurs during the addition of HBr
4. Which of the following compounds would produce a single product when treated with Cl2 in the presence of
ultraviolet radiation?
a. butane
b. 2-methylpropane
c. 2,2,-dimethylpropane
d. All would produce multiple products.
How many transition states are involved?
a. 2 b. 3
5. In the formation of an addition polymer such as polyvinylchloride,
c. 4 d. 5
a. the monomers must have at least one degree of unsaturation.
b. the formation occurs via a polar reaction.
c. the products have the same degree of complexity as biopolymers.
d. the resulting polymer generally contains two types of monomer.
6. Which of the following could act as a nucleophile?

a. HCl b. CH3NH2
c. BF3 d. CH3Br
7. A reaction that establishes equilibrium with almost no reactants present:

a. is exergonic.
b. has a negative ΔG°.
c. has a large Keq.
d. all of the above.
Name: Class: Date:
10. Examine the following biological reaction. 12. Consider a reaction with the following thermodynamic properties.
ΔH° = 77.7 kJ
ΔS° = –35.7 J/(K • mol)
ΔG°= 88.4 kJ
This reaction:
a. will be spontaneous at low temperatures.
b. has bonds in the products that are weaker than the reactants.
c. may have fewer and more complicated molecules in the product.
d. will proceed very slowly.
13. Which of the following does not characterize a more highly substituted carbocation?
In this reaction, which of the following is not indicated? a. forms more rapidly than less highly substituted carbocations
a. The reaction produces three products. b. forms product more rapidly than less highly substituted carbocations
b. Isocitrate is the primary reactant. c. has a larger ΔG± than less highly substituted carbocations
c. Isocitrate dehydrogenase is the catalyst for the reaction, d. is more stable than less highly substituted carbocations
d. NAD+ is an abbreviation for a required reactant. e. All of these characterize a highly substituted carbocation.
e. All indicate the conditions of the reaction.
14. If the following compound were dissolved in ether and treated with HCl, which of the following describes the
11. Consider the following process. product(s) of the reaction?
Which of the following correctly applies?

a. termination step b. unsymmetrical bond formation
c. polar reaction d. produces a radical
a. 3-bromoheptane
b. 4-bromoheptane
c. a mixture of 3-bromoheptane and 4-bromoheptane
Name: Class: Date:
15. What product forms when the following substance is treated with chloroform in the presence of KOH?
a. b.
c. d.
Name: Class: Date:
16. If the following compound was dissolved in ether and treated with HBr, which of the following describes the
major product(s) of the reaction? 17. Hydrogenation reactions use a metal catalyst as depicted below.
Which of the following does not occur during such a reaction?

a. The metal provides a surface upon molecules can adsorb.
b. π bonds are involved in the interaction between the metal and the unsaturated hydrocarbon.
a. c. Molecular hydrogen attacks the topside of the adsorbed hydrocarbon.
d. Hydrogen atoms are transferred to the carbon atoms of the multiple bond one at a time.
18. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.
b.
c.
Which atom is the most likely to be attacked by a nucleophile?

a. 1 b. 2
c. 3 d. 4
d. a mixture of and
Name: Class: Date:
19. Examine the following reaction. 23. Consider the following molecular model.
Which of the following is not indicated by this representation?

a. KI is the solvent
b. Cyclohexene is the reactant of interest.
c. The reaction is carried out at room temperature.
d. The reaction occurs in solution. I
Which of the following could be used to synthesize this compound?
e. All indicate the conditions of the reaction.
a.
20. Which of the following is a carbene?

a. R3C+ b. R:–
c. R2: d. R.
b.
21. A reaction has ΔH° = –14.7 kJ and ΔS° of 35.7 J/(K • mol), will
a. be exergonic. b. have a positive ΔG°.
c. have a very small Keq. d. will proceed rapidly.
c.
22. Which of the following is a difference between hydroboration/oxidation and oxymercuration?
a. conversion of an alkene to an alcohol b. Markovnikov regiochemistry
c. hydration d. heteroatom-containing intermediate
d. Either or
e. Any of the above
Name: Class: Date:
24. Consider partial hydrogenation of the following substance.

Which of the following describes this reaction?

a. 4 moles of hydrogen would required.
Which step is probably the slowest?
b. The product would contain trans double bond(s). a. A - C b. C - E
c. The product would be saturated. c. E - G d. G - I
d. The product would lower blood cholesterol.
e. All of the above would occur. 27. Consider the following energy diagram.
25. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.
Which step has the least endergonic ΔG±?

Which atom is the most electron poor? a. A - C b. C - E
a. 1 b. 2 c. E - G d. G - I
c. 3 d. 4
Name: Class: Date:
28. Which of the following will produce only one product upon dehydration? 30. The following shows the connectivity of atoms only. Atoms other than carbon and hydrogen are labeled.
a.
b.
c.
How many degrees of unsaturation are present in the compound?

a. 1
d.
b. 2
c. 3
d. 4
e. 5
e. b and d
f. a, b, and c
g. None produce a single product.
31. Povidone is produced commercially as a series of products having mean molecular weights ranging from
about 10,000 to 700,000. Complexed with iodine, povidone yields an iodophor, marketed under the tradename
29. In a polar reaction mechanism, the atom that gives away electrons in a neutral nucleophile will end up as a(n): Betadine, which is used as a topical anti-infective.
a. cation b. anion
c. radical d. neutral molecule
Identify the monomer unit(s) in povidone.
Name: Class: Date:
Exhibit 8-1
32. Name the following alkene and draw its line bond formula. To answer the question(s) below consider the following reaction:
When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed.
36. Refer to Exhibit 8-1. Provide the IUPAC name for the product of the reaction of cyclohexene with chlorine.
Exhibit 7-4
Provide names for each structure below. Be sure to include the cis, trans or E, Z designations where applicable.
Exhibit 7-6 37. Name:

MATCH each alkene below with the appropriate heat of hydrogenation. Place the letter of the correct answer in
the blank to the left of the alkene.
a. 125.9 kJ/mol
b. 118.4 kJ/mol
c. 115.5 kJ/mol
Exhibit 8-4
33. ______
Consider the reaction below to answer the following question(s).
When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed.

Exhibit 7-4
Provide names for each structure below. Be sure to include the cis, trans or E, Z designations where applicable.
34. Name:
35. Draw the mechanism of the hydration of 2-methyl-propene.
Name: Class: Date:
38. Refer to Exhibit 8-4. In the reaction of an alkene with dichlorocarbene, the dichlorocarbene is the:
a. electrophile. 41.
b. Lewis base.
c. nucleophile.
d. both b and c.
Exhibit 6-9
Use the reaction energy diagram below to answer the following question(s).
Exhibit 7-11
Predict the major organic product for each reaction below.
39.
Exhibit 8-3
Consider the reaction below to answer the following question(s).
42. Refer to Exhibit 6-9. The reactants are found at point _____ on the diagram.
Alkenes may be hydrated by the hydroboration/oxidation procedure shown.
Exhibit 8-7
Choose the best reagent from the list below for carrying out each transformation. Place the letter of the reagent in
the blank to the left of the reaction.
a. 1. O3 e. 1. OsO4
2. Zn, H3O+ 2. NaHSO3, H2O
40. Refer to Exhibit 8-3. Hydroboration/oxidation of alkenes occurs with: b. 1. BH3, THF f. KMnO4, acid
2. H2O2, NaOH, H2O
a. anti stereochemistry.
b. trans stereochemistry. c. CHCl3, KOH g. CH2I2, Zn(Cu)
c. syn stereochemistry.
d. unpredictable stereochemistry. d. H2O, H2SO4, heat h. 1. Hg(OAc)2, H2O
2. NaBH4
Exhibit 6-5
Add curved arrows to the following reactions to indicate the flow of electrons in each.
Name: Class: Date:
Drawing Instructions: Draw structures corresponding to each name below. Line structures should be used.
43. _____
49. Draw: (3E)-3,7-dimethyl-1,3,6-octatriene
44. Hydration of 4-methyl-1-pentene in the presence of an acid catalyst produces a product that is optically
inactive. Briefly explain why. 50. Draw the structure of atropine from the Atropa belladonna plant. List and identify all functional groups present.
Exhibit 8-6
Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
45.
Exhibit 7-11
Predict the major organic product for each reaction below.
46.
Exhibit 8-8
For each reaction below suggest structures for alkenes that give the indicated reaction products. There may be
more than one answer in some cases.
47.
Exhibit 7-1
Calculate the degree of unsaturation in each formula below. Show your calculations.
48. diazepam (Valium), C16H13N2OCl


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Name: Class: Date:

Which step has the least energetic transition state?

***ITEMS 31, 33-50 should be answered on the sheet itself. c. d.

9. Consider the following energy diagram for an enzyme-catalyzed reaction.

Which is applicable to this structure?

6. Which of the following could act as a nucleophile?

7. A reaction that establishes equilibrium with almost no reactants present:

Which of the following correctly applies?

Which of the following does not occur during such a reaction?

Which atom is the most likely to be attacked by a nucleophile?

Which of the following is not indicated by this representation?

20. Which of the following is a carbene?

e. Any of the above

24. Consider partial hydrogenation of the following substance.

Which of the following describes this reaction?

Which step has the least endergonic ΔG±?

How many degrees of unsaturation are present in the compound?

Identify the monomer unit(s) in povidone.

Exhibit 7-6 37. Name:

When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed.

35. Draw the mechanism of the hydration of 2-methyl-propene.

48. diazepam (Valium), C16H13N2OCl

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