Chapter Seven

MULTIPLE CHOICE QUESTIONS

Topic: Nomenclature; Stereochemistry

Topic: Nomenclature Section: 4.3, 4.5, 7.2
Section: 4.3, 4.5, 7.2 Difficulty Level: Medium
Difficulty Level: Easy
Name the following compound:
1. The correct IUPAC name for the following3.compound is:
Br HO

A) 2-Bromo-4-methylenehexane
A) (E)-4-phenyl-4-methylbut-3-en-1-ol
B) 2-(2-Bromopropyl)-1-butene
B) (E)-4-phenylpent-3-en-1-ol
C) 4-Bromo-2-ethyl-1-pentene
C) (Z)-4-phenylpent-3-en-1-ol
D) 2-Bromo-4-ethyl-1-pentene
D) (Z)-4-phenyl-4-methylbut-3-en-1-ol
E) 2-Bromo-4-ethyl-4-pentene
E) (E)-4-benzylpent-3-en-1-ol
Ans C
Ans B
:
:
Topic: Nomenclature; Stereochemistry
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
Difficulty Level: Medium
Name the following compound:
OCH3 Which structure represents (Z)-4-bromohexa-1,
2.
4.
A) Br

B)
A) (cis)-3-methoxyhex-3-ene
B) (Z)-4-methoxyhex-4-ene Br
C) (Z)-3-methoxyhex-3-ene C)
D) (E)-3-methoxyhex-3-ene
E) 3-methoxyhex-3-ene Br
Ans C D) Br
:

E) None of the above

Ans C
:

130
 Which structure represents (Z)-1,4-dichlorohex-
6.
A)
Topic: Nomenclature; Stereochemistry Cl
Section: 4.3, 4.5, 7.2 Cl
Difficulty Level: Medium B) Cl Cl

Which structure represents (E)-1-bromo-2-methylhex-2-ene?

5. C) Cl
A) Br
Cl
D) Cl
B) Br

Cl
C) E) None of the above
Ans B
Br :
D) Br

E) None of the above

Ans A
: Topic: Nomenclature
Section: 4.5, 7.2
Topic: Nomenclature; Stereochemistry Difficulty Level: Easy
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium 7. A correct IUPAC name for the following compou

A) 3,3,5-trimethyl-2-hexene
B) 3-isobutyl-3-isopropyl-2-propene
C) 3-isobutyl-4-methyl-2-pentene
D) 3-(1-methylethyl)-5-methyl-2-hexene
E) None of the above
Ans E
:

Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy

131
 8. The correct IUPAC name for the following
Section:
compound4.5, is:
7.2
Difficulty Level: Medium

10. The correct IUPAC name for the following comp

Cl

A) 4,5-Dimethyl-3-propyl-2-hexene Br
B) 4,5-Dimethyl-3-propyl-1-hexene
C) 3-(2,3-Dimethylpropyl)-1-hexene
D) 2,3-Dimethyl-4-isopropyl-5-hexene A) (E)-2-Bromo-3-chloro-5-methyl-2-hexene
E) 2,3-Dimethyl-4-propyl-5-hexene B) (E)-2-Bromo-3-chloro-5-methyl-3-hexene
Ans B C) (Z)-2-Bromo-3-chloro-5-methyl-3-hexene
: D) (Z)-2-Bromo-3-chloro-5-methyl-2-hexene
E) (E)-2-Methyl-5-bromo-4-chloro-4-hexene
Ans A
:

Topic: Nomenclature
Section: 4.5, 7.2 Topic: Nomenclature; Stereochemistry
Difficulty Level: Easy Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
9. Select the structure of 4ethyl-2,3-dimethyl-2-heptene.
A) Name the following compound:
11. Br

B)

A) (S,Z)-3-bromo-4-methylhex-2-ene
C) B) (S)-3-bromo-4-methylhex-2-ene
C) (S,Z)-4-bromo-3-methylhex-4-ene
D) (S,E)-3-bromo-4-methylhex-2-ene
E) (R,E)-3-bromo-4-methylhex-2-ene
D) Ans A
:

Topic: Nomenclature; Stereochemistry

E) Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium

Ans B
:

Topic: Nomenclature

132
 Name the following compound: Which structure represents (R,Z)-5-methylhept-
12. Br 14.
A)
Br

A) (S,E)-2,4-dibromo-3-methylpent-2-ene B)
B) (R,Z)-2,4-dibromo-3-methylpent-2-ene
C) (R,E)-2,4-dibromo-3-methylpent-3-ene C)
D) (S,E)-2,4-dibromo-3-methylpent-3-ene
E) (R,E)-2,4-dibromo-3-methylpent-2-ene
Ans E D)
:

E) None of the above

Topic: Nomenclature; Stereochemistry Ans D
Section: 4.3, 4.5, 5.7, 7.2 :
Difficulty Level: Hard

Name the following compound: Topic: Nomenclature; Stereochemistry

13. Section: 4.3, 4.5, 4.6, 5.7, 7.2
Difficulty Level: Medium

OH Name the following compound:

15. Cl

A) (R,Z)-5-phenyloct-5-en-3-ol
B) (R,Z)-5-benzyloct-5-en-3-ol
C) (R,E)-5-phenyloct-5-en-3-ol
D) (R,E)-5-benzyloct-5-en-3-ol
A) (S,E)-3-chlorohex-4-en-1-yne
E) (R,E)-5-benzyloct-3-en-6-ol
B) (R,E)-3-chlorohex-2-en-5-yne
Ans B
C) (S,E)-3-chlorohex-2-en-5-yne
:
D) (R,E)-3-chlorohex-4-en-1-yne
E) (R,E)-3-chloropent-4-en-1-yne
Topic: Nomenclature; Stereochemistry
Ans D
Section: 4.3, 4.5, 5.7, 7.2
:
Difficulty Level: Hard

133
Topic: Alkene Stability, Heats of 18. Which alkene would liberate the most heat per
Hydrogenation and Combustion hydrogenation?
Section: 7.3 A)
Difficulty Level: Easy B)
C)
16. Which molecule would have the lowest heat of hydrogenation?
D)
E)
Ans A
I II III IV : V
A) I
B) II
C) III
D) IV Topic: Alkene Stability, Heats of
E) V Hydrogenation and Combustion
Ans A Section: 7.3
: Difficulty Level: Easy

19. Which alkene is most stable?

Topic: Alkene Stability, Heats of
Hydrogenation and Combustion
Section: 7.3 I II III IV
Difficulty Level: Easy
A) I
17. Heats of hydrogenation data would be usefulB)in IIcomparing the relative stabilities
of which of the following substances? C) III
D) IV
E) V
Ans A
I II III IV : V
A) I, II, III
B) III, IV
C) I, II, V
D) Heats of hydrogenation data would not be a useful way to compare relative
stabilities of any of the substances.
E) All of the above substances could effectively be compared using heats of
hydrogenation data.
Ans C
:

Topic: Alkene Stability, Heats of

Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy

134
Topic: Alkene Stability, Heats of 22. Your task is to convert 2-bromobutane to 1-bute
Hydrogenation and Combustion reagents would you use?
Section: 7.3 A) KOH/H2O
Difficulty Level: Medium B) KOH/CH3OH
C) CH3ONa/CH3OH
20. Concerning the relative stabilities of alkenes,D)which
CH3CHis a2ONa/CH
false statement?
3CH2OH
A) Unless hydrogenation of the alkenes gives the E) same
(CH3)alkane,
3COK/(CH heats
3)3COH
of
hydrogenation cannot be used to measure their Ans relative
E stabilities.
B) In general, the greater the number of alkyl groups : attached to the carbon atoms
of the double bond, the greater the stability of the alkene.
C) The greater the quantity of heat liberated on combustion or hydrogenation of an
alkene, the greater its energy content.
D) trans-Cycloalkenes are always more stable Topic:
thanAlkene
the Synthesis
E) Heats of combustion can be used to measure Section:
the7.6
relative stabilities of isomeric
alkenes, even though their hydrogenation Difficulty
products Level:
are not
Easyidentical.
Ans D
: 23. What is the major product for the following reac
EtOH, EtONa
Topic: Alkene Synthesis, Reaction heat
Mechanisms OTs
Section: 7.6
Difficulty Level: Easy A) CH3CH2(CH3)C=CHCH3
B) CH3CH2(CH3)CHCH=CH2
21. Which product (or products) would be formed inCH
C) 3CH2(CH3)CHCH(OCH
appreciable 2CH3)CH3
amount(s) when
trans-1-bromo-2-methylcyclohexane undergoesD) None of the above
dehydrohalogenation upon
treatment with sodium ethoxide in ethanol? E) No reaction
Ans A

I II III IV

A) I
B) II
C) III
D) IV
E) More than one of these
Ans B
:

Topic: Alkene Synthesis

Section: 7.6
Difficulty Level: Easy

135
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 7.6 Section: 7.6
Difficulty Level: Easy Difficulty Level: Easy

24. What is the major product for the following reaction?

25. What is the major product for the following reac
t-BuOH, t-BuOK t-BuOH, t-BuOK
I
Cl

A) A)

Ot-Bu
B)
B)

C)

D) C)

E)

D)
Ans E
:

E)
None of the above
Ans D
:

136
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 7.6 Section: 7.6
Difficulty Level: Easy Difficulty Level: Easy

26. What is the major product for the following reaction?

27. What is the major product for the following reac
Cl
EtONa, EtOH EtOH, EtONa
I
heat heat

A)
A)

B)
B)

C)

C)
D)

D)
E)

E) None of the above Ans A

Ans A :
:

137
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 7.6 Section: 7.6
Difficulty Level: Easy Difficulty Level: Medium

28. What is the major product for the following reaction?

29. What is the major product for the following reac
Br
t-BuOK, t-BuOH EtONa, EtOH
Br
heat

A)
A)

B)
B)

C)

C)
D)

D)
E)

Ans E E) More than one of the above

: Ans C
:

138
Topic: Alkene Synthesis, Nomenclature, Topic: Alkene Synthesis
Reaction Mechanisms Section: 7.6
Section: 7.6 Difficulty Level: Hard
Difficulty Level: Medium
32. What is the major product for the following reac
30. Dehydrohalogenation of tert-pentyl bromide will produce 2-methyl-1-butene as
EtOH, EtONa
the chief product when:
A) CH3COONa is employed as the base. heat
B) KOH/C2H5OH is employed as the base. Cl
C) CH3CH2ONa/CH3CH2OH is employed as the base.
D) A)
(CH3)3COK/(CH3)3COH is employed as the base.
E) any base is used, as long as the temperature is sufficiently high.
Ans D
OEt
:
B)
Topic: Alkene Synthesis
Section: 7.6
C)
Difficulty Level: Hard

D)
31. What is the major product for the following reaction?
EtOH, EtONa
E)

Br
heat
Ans B
:
A)

OEt
B)

C)

D)

E)

Ans C
:

139
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 6.5, 7.6 Section: 6.5, 7.6
Difficulty Level: Medium Difficulty Level: Hard

33. What is the major product for the following reaction?

34. What is the major product for the following reac
1. NaI, acetone 1. NaI, acetone

2. t-BuOH, t-BuOK 2. t-BuOH, t-BuOK

OTs Cl

A) A)
B)
B)
C)
C)
D)
D)
E)
E)
Ans C
: Ans D
:

140
 Topic: Alkene Synthesis
Topic: Alkene Synthesis Section: 6.5, 7.6
Section: 6.5, 7.6 Difficulty Level: Hard
Difficulty Level: Hard
36. What is the major product for the following reac
35. What is the major product for the following reaction? 1. NaI, acetone
1. NaI, acetone
2. EtONa, EtOH, heat
Br
2. NaOH, EtOH, heat
Cl
A)
A)
B)
B)

C)
C)
D)
D)
E)
E)
Ans B
Ans C :
: Topic: Alkene Synthesis, Reaction
Mechanisms
Section: 6.5, 6.16, 7.6
Difficulty Level: Medium

37. Which compound listed below would you expec

2-bromo-2-methylbutane is refluxed with KOH/e
A) OH

B)
O
C)

D)

E)

Ans D
:

141
Topic: Alkene Synthesis 40. What is the major product of the reaction,
Section: 7.6B (CH3)3COK
Difficulty Level: Easy ?
(CH3)3COH
38. Zaitsev's rule states that: Br heat
A) In electrophilic addition of an unsymmetrical reagent to an unsymmetrical
A) (CH
alkene, the more positive portion of the reagent )2C=C(CH
will 3become 3)2
attached to the
carbon of the double bond bearing the greater B) number
(CH3)3CCH=CH
of hydrogen 2 atoms.
B) An equatorial substituent in cyclohexane resultsC) (CHin a3)more
2C=CHCH
stable3 conformation

than if that substituent were axial. D) (CH3)2C=CHCH2CH3

C) E2 reactions occur only if the -hydrogen and E) leaving
None ofgroupthesecan assume an
anti-periplanar arrangement. Ans B
:
D) When a reaction forms an alkene, and several possibilities exist, the more (or
most) stable isomer is the one which predominates.
Topic: Alkene
E) The order of reactivity of alcohols in dehydration Synthesis,
reactions is 3 > Reaction
2 > 1.
Ans D Mechanisms
: Section: 7.6C
Difficulty Level: Easy
Topic: Alkene Synthesis
Section: 7.6C 41. Which compound would be the major product?
Difficulty Level: Easy Br (CH3)3COK
?
(CH3)3COH
39. Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is
incorrect to state that: heat
A) this base is more effective than ethoxide ion, because itO(KO-
A)
basic of the two.
B) it tends to give the anti-Zaitsev, i.e., Hofmann, product.
C) it is more reactive in dimethyl sulfoxide than it is in
D) it favors E2 reactions over competing S B)
E) it will form, predominantly, the more stable alkene.
Ans: E
C)
Topic: Alkene Synthesis, Reaction
Mechanisms
Section: 7.6C D) OH
Difficulty Level: Easy
E)

Ans E
:

142
Topic: Carbocation Stability, Topic: Alkene Synthesis; Alcohol
Rearrangement Dehydration
Section: 7.7 Section: 7.7
Difficulty Level: Easy Difficulty Level: Easy

42. Which statement(s) is/are true of acid-catalyzed

44. Which
alcoholone
dehydrations?
of the following alcohols would dehy
A) Protonation of the alcohol is a fast step. with sulfuric acid?
B) Formation of a carbocation from the protonated alcohol is a slow step.
C) Rearrangements of less stable carbocations to more stable carbocations are
common. OH OH
D) Loss of a proton by the carbocation is a fast step. I II
E) All of the above
Ans E O
: OH
IV V
Topic: Alkene Synthesis, Reaction A) I
Mechanisms B) II
Section: 7.7 C) III
Difficulty Level: Easy D) IV
E) V
Ans B dehydration of 2-methyl-
43. Which product(s) would be produced by acid-catalyzed
2-pentanol? :

A)

B)
and

C)
and

D)

E)
O
Ans B
:

143
Topic: Alkene Synthesis; Alcohol Topic: Alkene Synthesis; Alcohol
Dehydration Dehydration
Section: 7.7 Section: 7.7
Difficulty Level: Easy Difficulty Level: Easy

45. Which mechanistic step in the acid-catalyzed

46.dehydration
Which alcohol
of 3,3-dimethyl-2-
would be most easily dehydrated
butanol is the rate determining step? A) CH3
A) Step 1:
CH CH CCH CH
3 2 2 3

+ H3O+ + H2O OH
OH OH2 B) CH3
B) Step 2:
CH3CH2CHCHCH3
+ H2O OH
OH2 C) CH3
C) Step 3: CH3CH2CHCH2CH2OH
D) CH3
HOCH2CHCH2CH2CH3
D) Step 4a: E) CH2OH
+
+ H2O + H3OCH 3CH2CHCH2CH3
Ans A
E) Step 4b: :
+ H2O + H3O+

Ans B
:

144
Topic: Alkene Synthesis; Alcohol Topic: Carbocation Stability
Dehydration Section: 7.7
Section: 7.7 Difficulty Level: Medium
Difficulty Level: Easy
48. Which alcohol would initially produce the most s
47. Which alcohol would be most easily dehydrated?
with concentrated H2SO4?
A) OH

B)
OH OH OH
I II III
OH
OH
C)OH
IV V OH
A) I D)
B) II HO
C) III
D) IV E) HO
E) V
Ans B
:
Ans A
:

Topic: Carbocation Stability,

Rearrangement
Section: 6.10, 6.17, 7.7
Difficulty Level: Hard

49. Carbocations are frequent intermediates in acid

etc. What do carbocations usually do? They m
A) rearrange to a more stable carbocation.
B) lose a proton to form an alkene.
C) combine with a nucleophile.
D) react with an alkene to form a larger carbocatio
E) do all of the above.
Ans E
:

145
Topic: Carbocation Stability, 51. Neopentyl alcohol, (CH3)3CCH2OH, cannot be d
Rearrangement rearrangement. What is the chief product of de
Section: 6.11B, 7.7B
Difficulty Level: Easy
I
50. Which of the following carbocations would NOT be likely to undergo II III
rearrangement?
A) CH3CHCHCH3
CH3
B) CH3 IV V
CH3CHCCH3 A) I
CH3 B) II
C) CH3 C) III
D) IV
CH3CCH2CH3
E) V
D) CH3 Ans B
CH3CHCH2 :
E) CH3
CH3CCHCH2CH3
CH3 Topic: Carbocation Stability,
Ans C Rearrangement
: Section: 5.12, 6.10, 6.17, 7.8
Difficulty Level: Medium
Topic: Carbocation Stability,
Rearrangement 52. What is the major product of the reaction betwe
Section: 7.8 bromo-3-methylpentane at room temperature?
Difficulty Level: Hard A)

B) OCH3

C)

D)
H3CO
E) Both A) and C)
Ans D
:

Topic: Carbocation Stability,

Rearrangement
Section: 6.10, 6.17, 7.8
Difficulty Level: Easy

146
 53. Rearrangements are likely to occur in which
Topic:
of Alkene
the following
Synthesis
reaction types?
A) SN1 reactions Section: 6.10, 6.17, 7.8
B) SN2 reactions Difficulty Level: Easy
C) E1 reactions
D) E2 reactions 55. What is the major product for the following reac
E) Both SN1 and E1 reactions
Ans E EtOH, heat
Br
:
Topic: Carbocation Stability,
Rearrangement
Section: 6.10, 6.17, 7.8 A)
Difficulty Level: Easy

54. What is the major product of the reaction of the following reaction?
I
ethanol, 20 oC B)

A) C)
CH3CH2O

B) OCH2CH3 D)

C)
E) More than one of the above
Ans E
:
D)

E) More than one of the above

Ans A
:

147
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 6.10, 6.17, 7.8 Section: 6.10, 6.17, 7.8
Difficulty Level: Medium Difficulty Level: Medium

56. What is the major product for the following reaction?

57. What is the major product for the following reac
Cl
EtOH, heat EtOH, heat
I

A)
A)

B)
B)

C)

C)
D)

D)
E)

E) None of the above Ans D

Ans C :
:

148
Topic: Carbocation Stability, Topic: Carbocation Stability,
Rearrangement Rearrangement
Section: 6.10, 6.17, 7.8 Section: 6.10, 6.17, 7.8
Difficulty Level: Hard Difficulty Level: Hard

58. What is the major product of the reaction of59.

the What
following
is the
reaction?
major product of the reaction of the
Cl
EtOH, heat
EtOH, heat

A) OTs

A)
B)

C) OEt B)

D)
C)

E)
OEt
D)
Ans D
:

E) None of the above

Ans A
:

149
Topic: Carbocation Stability, Topic: Carbocation Stability,
Rearrangement Rearrangement
Section: 6.10, 6.17, 7.8 Section: 4.16, 6.10, 6.17, 7.3, 7.8
Difficulty Level: Hard Difficulty Level: Medium

60. What is the major product of the reaction of61.

the What
following
is the
reaction?
major product of the reaction of the
Br
CH3OH, heat 1. H2, Ni

Cl 2. EtOH, heat

A) A)

H3CO B)
B)
C)

C)
D) OEt

D)
E) A mixture of A) and B)
Ans C
E) :

Ans E
:

150
Topic: Alkene Synthesis, Reaction Topic: Alkene Synthesis, Reaction
Mechanisms, Carbocation Mechanisms, Carbocation
Rearrangements Rearrangements
Section: 7.7, 7.8 Section: 7.7, 7.8
Difficulty Level: Medium Difficulty Level: Hard

62. Which alkene would you expect to be the major

63. What
product
willofbethe
thefollowing
major product of the following r
dehydration? 85% H3PO4
?
H2SO4 heat
?
heat OH
OH A)

B)
I II III

C)

IV V
D) O

A) I E)
B) II
C) III Ans A
D) IV :
E) V
Ans C
:

151
Topic: Alkene Synthesis, Nomenclature Topic: Alkyne Synthesis
Section: 7.6C, 7.7, 7.10 Section: 3.6, 7.11, 7.12
Difficulty Level: Medium Difficulty Level: Hard

64. Which of the following reactions would yield66.

3,3-dimethyl-1-butene
Which reaction conditions
in a would not yield 2-but
reasonable percentage yield (i.e., greater than
A) 50%)?
a. EtONa, EtOH
A) H2SO4
b. CH3I
heat
OH B) a. CH3Li, THF
B) (CH3)3COK, (CH3)3COH
b. CH3I
heat
Br C) a. NaNH2, NH3 (liq)
C)
i) 3 NaNH2, mineral oil, heat b. CH3I
Br D) a. NaCH2CH3, THF
ii) H O+
3
Br
D) All of these b. CH3I
E) Answers B) and C) only E) More than one of these
Ans B Ans A
: :

Topic: Alkyne Synthesis Topic: Alkene Synthesis, Nomenclature,

Section: 7.11 Reaction Mechanisms
Difficulty Level: Easy Section: 7.6, 7.7, 7.11, 7.12
Difficulty Level: Easy
65. Which reaction would yield 2-butyne?
A) CH3CC:Na + CH3Br 67. Which of the following reactions would yield 2-p
B) CH3CH2Br + HCC:Na A) NaNH2 I
C) CH3:Na + HCCCH3
(1 mol)
D) More than one of these
E) None of these B) NaNH2 Br
Ans A (1 mol)
: C) Br
CH3OH

Br
D) HA
heat
OH
E) Br
NaOC2H5
C2H5OH
Ans B
:

152
Topic: Alkyne Synthesis Topic: Alkyne Synthesis
Section: 7.10, 7.11, 7.12 Section: 7.11, 7.12
Difficulty Level: Medium Difficulty Level: Medium

68. Which of the following methods could be used

70. toWhich
synthesize
reaction
4,4-dimethyl-2-
would not result in alkylation of
hexyne? A) Br
A) CH3 Li
C2H5 C C C: Na H3C I B) Cl
CH3 Li
B) CH3 C)
H3C C C: Na C2H5 C Br
CH3
Br
C) Li
NaNH2 ( excess)
D)
NH3 (l) OTs
Br Br Li
D) More than one of these E) None of the above
E) None of these Ans C
Ans D :
:
Topic: Alkyne Synthesis
Topic: Alkyne Synthesis Section: 7.11, 7.12
Section: 7.11, 7.12 Difficulty Level: Medium
Difficulty Level: Easy
71. Which reaction would not primarily proceed via
69.Which statement is/are true about acetylide anions?
A) Br
A)They do not alkylate with secondary alkyl halides. Li
B)Primary alkyl halides are best suited for alkylation.
B) Cl
C)In the presence of tertiary alkyl halides, the acetylide anion Li
acts as base to give
an elimination product. C)
D) Only two of the above are true.
E) All of the statements are true.
Ans E Br
Li
: D)
OTs
Li
E) All of them proceed via SN2
Ans C
:

153
Topic: Alkene/Alkyne Reactions, Topic: Index of Hydrogen Deficiency,
Reaction Mechanisms Catalytic Hydrogenation
Section: 3.16, 7.13 Section: 2.16, 4.16, 4.17, 7.13
Difficulty Level: Easy Difficulty Level: Easy

72. Which would be the major product of the following

74. A compound
reaction sequence?
X with the formula C7H10 undergoe
1a. NaNH2, NH3 (liq.) produce a compound Y with the formula C7H14.
1b. T3O + A) X might have one triple bond and one ring.
B) X might have two double bonds and one ring.
2. H2, Pd/C C) X might have one double bond and two rings.
D) X might have one double bond and one triple bo
A) E) More than one of the above
Ans E
:
CH2CH3
B) Topic: Index of Hydrogen Deficiency,
Catalytic Hydrogenation
CH=CHT Section: 2.16, 4.16, 4.17, 7.13
C) Difficulty Level: Medium

CH=CH2 75. A compound, C6H10, which reacts with 2 mol of

D) catalyst and which shows an IR absorption ban
could be:
CH2CH2T
E) None of the above
Ans D I II I
:

Topic: Structure Elucidation

Section: 2.16, 4.16, 7.13 IV V
Difficulty Level: Medium
A) I
73. An unknown compound, B, has the molecular B)formula
II C
hydrogenation 1 mol of B absorbs 2 mol of hydrogen
C) III and yields 2-
methylhexane. B has significant IR absorption
D) band
IV at about 3300 and 2200
-1
cm . Which compound best represents E) V
A) 3-methyl-1-hexyne Ans C
B) 5-methyl-2-hexyne :
C) 5-methyl-1,3-hexadiene
D) 5-methyl-1-hexyne
E) 2-methyl-1,5-hexadiene
Ans D
:

154
Topic: Index of Hydrogen Deficiency, Topic: Index of Hydrogen Deficiency,
Catalytic Hydrogenation Catalytic Hydrogenation
Section: 2.16, 4.16, 4.17, 7.13 Section: 4.16, 4.17, 7.13
Difficulty Level: Medium Difficulty Level: Easy

76. What is the structure of a compound with formula

78. C H2, Pt
-1 X (C H
at approximately 3300 cm and which can be catalytically reduced
8 14 ) witho Y (C8H16)
Given: 25 C
hydrogen to 2-methylpentane?
A) One can conclude that X has:
A) no rings and no double bonds.
B) B) no rings and one double bond.
C) one ring and one double bond.
C)
D) two rings and no double bonds.
E) one triple bond.
D) Ans C
:
E)
Topic: Index of Hydrogen Deficiency,
Catalytic Hydrogenation
Ans D Section: 4.16, 4.17, 7.13
: Difficulty Level: Easy

Topic: Index of Hydrogen Deficiency, 79. On hydrogenation, a compound C9H12 absorbs

Catalytic Hydrogenation following is a possible structure for the compou
Section: 4.16, 4.17, 7.13
Difficulty Level: Easy

77. Upon catalytic hydrogenation, a compound C I II III

hydrogen. Select a structure for C6H

IV V
I II III A)
IV I V
B) II
A) I, II C) III
B) III D) IV
C) II, III E) V
D) IV, V Ans D
E) I, IV, V :
Ans D
:

155
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 7.10A, 7.13 Section: 7.11, 7.12, 7.13
Difficulty Level: Medium Difficulty Level: Medium

80. What is the major product for the following reaction

82. Whatsequence?
is the major product for the following reac
1a. NaNH2 (excess) 1a. NaNH2, NH3 (liq.)
mineral oil, heat H 1b. CH3CH2CH2Br
Cl 1b. NH4Cl
H 2. H2 (excess), Pd/C
Cl
2. H2 (excess), Pd/C
A)
A) B)
C)
D) N
H
B) C E) None of the above
Ans B
C) :

Topic: Alkene Synthesis

D) Section: 7.11, 7.12, 7.13
Difficulty Level: Medium
E) None of the above
Ans E 83. What is the major product for the following reac
: 1a. NaNH2, NH3 (liq.)
Topic: Alkene/Alkyne Reactions, 1b. CH3CH2CH2Br
Reaction Mechanisms
Section: 3.16, 7.10A, 7.13 2. H2 (excess), Pd/C
Difficulty Level: Medium
A)
81. Which would be the major product of the following
B) CHreaction sequence?
3CH2CH2Br
1a. NaNH2 (excess)
Cl mineral oil, heat C)
Cl +
1b. T3O D)
H
2. H2, Pd/C
E) None of the above
Ans A
A) (CH3CH2)2C=C=CHT
:
B) (CH3CH2)2C=C=CH2
C) (CH3CH2)2CHCCT
D) (CH3CH2)2CHCH=CHT
E) None of the above
Ans E
:

156
Topic: Alkene Reactions, Reaction Topic: Alkene/Alkyne Reactions,
Mechanisms Reaction Mechanisms
Section: 4.16, 7.14A Section: 7.6, 7.14A
Difficulty Level: Medium Difficulty Level: Medium

84. Which would be the major product of the following

85. Which
reaction?
would be the major product of the followi
1. EtOH, EtONa
D2, Ni
?
2. D2, Pd/C
Br

D D CH3
A)
D CH3 H CH3 DD

H D H
I II B) III
CH3 D

DH D C) CH3

D H D
IV V D
H
A) I
B) II D)
C) III D
D) IV
H
E) V
Ans A D
: E)

D
D
Ans C
:

157
Topic: Alkene Synthesis, Nomenclature, Topic: Alkene Synthesis
Reaction Mechanisms Section: 7.10A, 7.15
Section: 7.6, 7.7, 7.15 Difficulty Level: Medium
Difficulty Level: Medium
88. What is the major product for the following reac
86. Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?
1a. NaNH2 (excess)
A) (CH3)2CHCCH3 + conc. H2SO4 mineral oil, heat
B) (CH3)2CHCCH + Li/liq.NH3 Cl 1b. NH4Cl
C) (CH3)2CHCH2CH2Br + CH3ONa/CH3 Cl
D) (CH3)2CHCHBrCH3 + (CH3)3COK/(CH 2. H2, P-2
E) (CH3)2CHCCH + H2/Ni2B (P-2)
Ans A A)
:

Topic: Alkene Synthesis

Section: 7.10, 7.15 B) C
Difficulty Level: Medium

C)
87. What is the major product for the following reaction sequence?
Br
1. NaNH2 (excess)
mineral oil, heat D)

2. H2, Pd/CaCO3 E) None of the above

Br quinoline Ans C
:
A)
B) Topic: Alkene Synthesis
C) Section: 7.11, 7.12, 7.15
D) Difficulty Level: Medium

89. What is the major product for the following reac

E)
1a. NaNH2, NH3 (liq.)
H 1b. CH3CH2CH2Br
Ans D H 2a. Li, CH3CH2NH2
:
2b. NH4Cl

A)
B)
C)
D) N
H
E) None of the above
Ans C
:

158
Topic: Alkene Synthesis Topic: Alkene Synthesis
Section: 7.11, 7.12, 7.15 Section: 7.11, 7.12, 7.15
Difficulty Level: Medium Difficulty Level: Medium

90. What is the major product for the following reaction

92. Whatsequence?
is the major product for the following reac
1a. NaNH2, NH3 (liq.) 1a. n-BuLi, THF
H 1b. CH3CH2CH2Br 1b. CH3CH2CH2Br

H 2. H2, Pd/CaCO3 2. H2, P-2

quinoline
A)
A) B) CH3CH2CH2Br
B)
C)
C)
D)
D) N
H
E) None of the above
Ans C E) None of the above
: Ans D
:
Topic: Alkene Synthesis
Section: 7.11, 7.12, 7.15 Topic: Alkene Synthesis, Nomenclature,
Difficulty Level: Medium Reaction Mechanisms
Section: 7.6, 7.7, 7.13, 7.15
Difficulty
91. What is the major product for the following Level:
reaction Easy
sequence?
1a. NaNH2, NH3 (liq.)
9 Which of these is the most satisfactory method for
1b. CH3CH2CH2Br
3. pentene?
2a. Li, CH3CH2NH2 A) CH3CHBrCH2CH2CH3 + (CH3)3COK/(CH3)3COH
2b. NH4Cl B) CH3CCCH2CH3 + H2, Pt
C CH3CCCH2CH3 + H2, Ni2B (P-2)
)
A) D CH3CCCH2CH3 + Li/liq. NH3
B) CH3CH2CH2Br )
C) E) CH3CH2CHBrCH2CH3 + CH3CH2ONa/CH3CH2OH
Ans: C
D)

E) None of the above

Ans C
:

159
Topic: Alkyne Synthesis, Nomenclature, Topic: Alkyne Synthesis, Catalytic
Reaction Mechanisms hydrogenation
Section: 7.6, 7.13, 7.15 Section: 7.11, 7.15A
Difficulty Level: Easy Difficulty Level: Medium

94. Which reaction would not be a method for preparing

96. The structure
5-methyl-1-hexyne?
of the product, C, of the following
A)
1) NaNH2 (2 mol), liq NH3 NaNH2 CH3CH2Br
Br +
A B
2) NH4 NH3(l)
B)
HC CNa + Cl A)
C)
+ HC CH B)
Li
D) 1) NaNH2 (3 mol), liq NH3
Br
C)
2) NH4+
Br
E) Br Br
1) NaNH2 (3 mol), liq NH3D)
Br
2) NH4+
Ans C
E)
:

Topic: Alkyne Reduction, Nomenclature,

Reaction Mechanisms Ans A
Section: 7.13, 7.15 :
Difficulty Level: Easy

Which of the following reductions of an alkyne is NOT correct?

95.
A) 2-Pentyne + 2H2/Pt pentane
B) 2-Pentyne + H2/Ni2B Z-2-Pentene
C) 2-Pentyne + Li/NH3(l) Z-2-Pentene
D) All of the above are correct.
E) None of the above is correct.
Ans C
:

160
Topic: Alkene/Alkyne Reactions, Topic: Alkene/Alkyne Reactions,
Reaction Mechanisms Reaction Mechanisms
Section: 7.13, 7.15A Section: 6.5, 6.16, 7.11, 7.15A
Difficulty Level: Medium Difficulty Level: Hard

97. Which would be the major product of the following

98. Which
reaction
wouldsequence?
be the major product of the followi
1. D2, Pd/CaCO3 1a. NaNH2, NH3 (liq.)
quinoline 1b. CH2=CHCH2Br

2. H2, Ni 2. D2, P-2

A)
A) D

D
D
D
B)
B) D D D H D
D
H
D D H
D
C) D
C)

D
D
D
D)
D)

E) None of the above

E) None of the above
Ans A
Ans B
:
:

161
Topic: Dissolving Metal Reduction; SHORT ANSWER QUESTIONS
trans-hydrogenation
Section: 7.15B Topic: General Information
Difficulty Level: Easy Section: 7.6B
Difficulty Level: Easy
99. The structure of the product obtained from 2-butyne and Li/C
A) 100. When an elimination reaction gives the most sta
we say that the elimination follows __________
Ans Zaitsev
B) :
C)
HN
Topic: General Information
Section: 7.6C
D) Difficulty Level: Easy
NH
101. When an elimination reaction gives the less sub
product, we say that the elimination follows ___
E)
Ans Hofmann
Ans A :
:
Topic: General Information
Section: 7.7
Difficulty Level: Easy

102. In a dehydration reaction, the leaving group is _

Ans a molecule of water
:

Topic: General Information

Section: 7.7
Difficulty Level: Easy

103. Dehydration of alcohols requires a __________

Ans strong acid
:

Topic: General Information

Section: 7.8
Difficulty Level: Medium

104. Carbocations have three options available for fu

include reaction with a nucleophile, loss of a be
________________.
Ans rearrangement
:

162
 Section: 7.15
Topic: General Information Difficulty Level: Medium
Section: 7.10
Difficulty Level: Medium 110. How will you prepare trans-2-heptene from 2-he
Ans Dissolving metal reduction with metallic N
105. Alkynes can be produced from either __________________
: or Na, NH3 (l)
_________________ dihalides.
Ans vicinal/geminal
: Topic: Nomenclature, Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Topic: General Information Difficulty Level: Hard
Section: 7.14
Difficulty Level: Easy 111. Draw the structures of all stereoisomers of 2-ch
showing all stereochemical details, using appro
106. In hydrogenation reactions, both hydrogen atoms add to the pietc.)
(dash-wedge, system from the
as relevant.
same face of the molecule. This is an example of
Ansa(n) _________ addition. 2-chloro-4-methyl-3
Ans syn :
: Cl H H C
Cl

Topic: Alkene Hydrogenation

Section: 7.14 (2R, 3E) (2S, 3E)
Difficulty Level: Easy
Topic: Alkene Nomenclature, Relative
107. How will you prepare cis-1,2-dimethylcyclohexane from 1,2-
Stability
dimethylcyclohexene?
Section: 4.5, 7.3
Ans Catalytic hydrogenation with H2
Difficulty Level: Hard
: H2, Ni
112. The ambiguous name dimethylcyclopentene do
between several structures.
Topic: General Information a) Draw the structures of all constitutional isom
Section: 7.15 b) Indicate which of these is likely to be the mo
Difficulty Level: Easy heat of
combustion, justifying your rationale briefly.
108. Syn hydrogenation of an alkyne will produce a _________
c) Which ofalkene.
these structures represents an ach
Ans Cis / Z Ans a)
: : dimethylcyclopentene

Topic: General Information

Section: 7.15
Difficulty Level: Medium
I II III IV
109. Conversion of alkynes to E-alkenes (trans-alkenes) can be accomplished via a
__________________ reaction. b) Structure I is likely to be the most stab
Ans dissolving metal reduction substituted
: alkene: II, IV and V are tri-substituted;
Topic: Alkyne Reduction c) Structure I is achiral

163
 Propose a two-step synthetic strategy for the sy
Topic: Carbocation Rearrangement, 114. 5-methyl-2-hexanol.
Alkene Synthesis, Dehydration Ans OH
Mechanism : H3O+
+
Section: 7.7 heat
Difficulty Level: Medium Step 1:
Acid-catalyzed dehydration of 5-methyl-2-
113. Provide a mechanistic explanation for the formation ofmixture
the observed products in
of 5-methyl-1-hexene and 5-meth
the following reaction. Step 2:
H3O+ Catalytic hydrogenation of the double bon
OH
heat 2-methylhexane

Ans H Topic: Carbocation Stability,

: Rearrangement OH
: :

:O H

:
1) OH 2 :O H
Section: 7.8

:
H Difficulty Level: Medium H

115. What new, more stable, carbocation(s) may b

rearrangement
2) OH2+ carbocation undergoes spontaneous rearrange
[-H2O]
:

Ans H
:
3a) :O H
:

:O H
H H via a Methyl (methide)
H shift via a Hydr
H
Both Topic: Alkyne Synthesis, Acid-Base
H
H H reactions H
Section: 7.10
3b) :O H Difficulty Level: Medium :O H
:

H H

Topic: Nomenclature, Multistep

Synthesis
Section: 4.16, 7.7
Difficulty Level: Hard

164
 116. Complete the following reaction sequence,117. providing
The IRa brief
spectrum
rationale
of anfor
unknown
your substance Q, C
answer. peaks at 3310 cm and 2140 cm-1. Treatment o
-1

O of Raney Ni affords nearly quantitative yields of

i) PCl5 a reasonable structure for Q, based on the abov
?
ii) 3 NaNH2, your rationale. Also give its IUPAC name.
Ans
mineral oil, heat H
: excess H2
iii) H3O+ Ni
Ans O Cl : Na
Cl
: PCl5 3 NaNH2, H3O+ -1
IR: 2140, 3310 cm 2,3-dime
mineral oil, heat
I (-2HCl) II Substance Q: 5,6-III
Reaction with PCl5 would afford a geminal dihalide I, which would undergo
dimethyl-1-heptyne
E2 elimination when heated, losing 2 moles of HCl to afford the alkyne III.
However, since III is a terminal alkyne, it has a hydrogen
The Indexatom that is labile
of Hydrogen deficiency of Q is
in presence of NaNH2; hence, an extra mole equivalent of the base
data suggests that Qisis a terminal alkyne;
required to ensure complete reaction and convert its structure. The catalytic hydrogenation d
III into the sodium alkynide intermediate, II; this,the upon acidification,
carbon skeleton.affords
Due to the specific s
the final alkyne product III. skeleton, there is only one possible positio
Thus, the structure given above is consist
information.
IUPAC Name: 5,6-dimethyl-1-heptyne

Topic: Nomenclature, Index of Hydrogen

Deficiency, IR Spectroscopy, Catalytic
Hydrogenation
Section: 2.16, 7.13
Difficulty Level: Medium

Topic: Nomenclature, Multistep

Synthesis

165
Section: 7.11, 7.12, 7.15
Difficulty Level: Medium

118. Propose a reasonable synthetic strategy for the synthesis of

heptene from 4-methyl-1-pentyne.
Ans NaNH2 Na+: CH3CH2Br
: NH3 (l)

Li, NH3(l)

Step 1:
Add NaNH2/NH3(l) to selectively deprotonate the alkyne hydrogen.
Step 2:
Add ethyl iodide to give 6-methyl-3-pentyne by an S
Step 3:
Add Na(s)/NH3(l) to give the desired
reduction.

Topic: Alkyne Synthesis, Alkyne

Hydrogenation
Section: 7.11, 7.12, 7.15A
Difficulty Level: Medium

119. Complete the following reaction, giving structural details of all intermediates as
well as the final product.

1) NaNH2, NH3 (l)

?
2) CH3CH2CH2Br
3) H2, Lindlar catalyst
Ans NaNH2
: NH3 (l) Na
:

CH3CH2CH2Br

H2
Lindlar catalyst

166