Chapter 7
Chapter 7
Chapter 7
Topic: Nomenclature
Section: 4.3, 4.5, 7.2
Difficulty Level: Easy
A) 2-Bromo-4-methylenehexane
B) 2-(2-Bromopropyl)-1-butene
C) 4-Bromo-2-ethyl-1-pentene
D) 2-Bromo-4-ethyl-1-pentene
E) 2-Bromo-4-ethyl-4-pentene
Ans: C
A) (cis)-3-methoxyhex-3-ene
B) (Z)-4-methoxyhex-4-ene
C) (Z)-3-methoxyhex-3-ene
D) (E)-3-methoxyhex-3-ene
E) 3-methoxyhex-3-ene
Ans: C
130
Difficulty Level: Medium
A) (E)-4-phenyl-4-methylbut-3-en-1-ol
B) (E)-4-phenylpent-3-en-1-ol
C) (Z)-4-phenylpent-3-en-1-ol
D) (Z)-4-phenyl-4-methylbut-3-en-1-ol
E) (E)-4-benzylpent-3-en-1-ol
Ans: B
131
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
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
A) 4,5-Dimethyl-3-propyl-2-hexene
B) 4,5-Dimethyl-3-propyl-1-hexene
C) 3-(2,3-Dimethylpropyl)-1-hexene
D) 2,3-Dimethyl-4-isopropyl-5-hexene
E) 2,3-Dimethyl-4-propyl-5-hexene
Ans: B
132
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Medium
10. The correct IUPAC name for the following compound is:
A) (E)-2-Bromo-3-chloro-5-methyl-2-hexene
B) (E)-2-Bromo-3-chloro-5-methyl-3-hexene
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
133
11. Name the following compound:
A) (S,Z)-3-bromo-4-methylhex-2-ene
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
Ans: A
A) (S,E)-2,4-dibromo-3-methylpent-2-ene
B) (R,Z)-2,4-dibromo-3-methylpent-2-ene
C) (R,E)-2,4-dibromo-3-methylpent-3-ene
D) (S,E)-2,4-dibromo-3-methylpent-3-ene
E) (R,E)-2,4-dibromo-3-methylpent-2-ene
Ans: E
134
13. Name the following compound:
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
E) (R,E)-5-benzyloct-3-en-6-ol
Ans: B
A) (S,E)-3-chlorohex-4-en-1-yne
B) (R,E)-3-chlorohex-2-en-5-yne
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
Ans: D
135
Difficulty Level: Easy
A) I
B) II
C) III
D) IV
E) V
Ans: A
17. Heats of hydrogenation data would be useful in comparing the relative stabilities of
which of the following substances?
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
136
18. Which alkene would liberate the most heat per mole when subjected to catalytic
hydrogenation?
A)
B)
C)
D)
E)
Ans: A
A) I
B) II
C) III
D) IV
E) V
Ans: A
137
20. Concerning the relative stabilities of alkenes, which is a false statement?
A) Unless hydrogenation of the alkenes gives the same alkane, heats of hydrogenation
cannot be used to measure their relative 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 than the cis-isomers.
E) Heats of combustion can be used to measure the relative stabilities of isomeric alkenes,
even though their hydrogenation products are not identical.
Ans: D
21. Which product (or products) would be formed in appreciable amount(s) when trans-1-
bromo-2-methylcyclohexane undergoes dehydrohalogenation upon treatment with
sodium ethoxide in ethanol?
A) I
B) II
C) III
D) IV
E) More than one of these
Ans: B
138
22. Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents
would you use?
A) KOH/H2O
B) KOH/CH3OH
C) CH3ONa/CH3OH
D) CH3CH2ONa/CH3CH2OH
E) (CH3)3COK/(CH3)3COH
Ans: E
A) CH3CH2(CH3)C=CHCH3
B) CH3CH2(CH3)CHCH=CH2
C) CH3CH2(CH3)CHCH(OCH2CH3)CH3
D) None of the above
E) No reaction
Ans: A
139
24. What is the major product for the following reaction?
A)
B)
C)
D)
E)
Ans: E
A)
B)
C)
D)
E)
None of the above
Ans: D
140
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
A)
B)
C)
D)
E) None of the above
Ans: A
A)
B)
C)
D)
E)
Ans: A
141
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: E
142
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Medium
A)
B)
C)
D)
E) More than one of the above
Ans: C
143
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Hard
A)
B)
C)
D)
E)
Ans: C
A)
B)
C)
D)
E)
Ans: B
144
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Medium
A)
B)
C)
D)
E)
Ans: C
145
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
A)
B)
C)
D)
E)
Ans: D
146
35. What is the major product for the following reaction?
A)
B)
C)
D)
E)
Ans: C
A)
B)
C)
D)
E)
Ans: B
147
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 6.5, 6.16, 7.6
Difficulty Level: Medium
37. Which compound listed below would you expect to be the major product when 2-
bromo-2-methylbutane is refluxed with KOH/ethanol?
A)
B)
C)
D)
E)
Ans: D
148
38. Zaitsev's rule states that:
A) In electrophilic addition of an unsymmetrical reagent to an unsymmetrical alkene, the
more positive portion of the reagent will become attached to the carbon of the double
bond bearing the greater number of hydrogen atoms.
B) An equatorial substituent in cyclohexane results in a more stable conformation than if
that substituent were axial.
C) E2 reactions occur only if the -hydrogen and leaving group can assume an anti-
periplanar arrangement.
D) When a reaction forms an alkene, and several possibilities exist, the more (or most)
stable isomer is the one which predominates.
E) The order of reactivity of alcohols in dehydration reactions is 3 > 2 > 1.
Ans: D
149
40. What is the major product of the reaction,
A) (CH3)2C=C(CH3)2
B) (CH3)3CCH=CH2
C) (CH3)2C=CHCH3
D) (CH3)2C=CHCH2CH3
E) None of these
Ans: B
A)
B)
C)
D)
E)
Ans: E
150
Topic: Carbocation Stability, Rearrangement
Section: 7.7
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: B
151
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.7
Difficulty Level: Easy
44. Which one of the following alcohols would dehydrate most rapidly when treated with
sulfuric acid?
A) I
B) II
C) III
D) IV
E) V
Ans: B
152
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.7
Difficulty Level: Easy
153
47. Which alcohol would be most easily dehydrated?
A) I
B) II
C) III
D) IV
E) V
Ans: B
48. Which alcohol would initially produce the most stable carbocation when treated with
concentrated H2SO4?
A)
B)
C)
D)
E)
Ans: A
49. Carbocations are frequent intermediates in acidic reactions of alkenes, alcohols, etc.
What do carbocations usually do? They may:
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 carbocation.
E) do all of the above.
Ans: E
154
Topic: Carbocation Stability, Rearrangement
Section: 6.11B, 7.7B
Difficulty Level: Easy
50. Which of the following carbocations would NOT be likely to undergo rearrangement?
A)
B)
C)
D)
E)
Ans: C
A) I
B) II
C) III
D) IV
E) V
Ans: B
52. What is the major product of the reaction between methanol and (2R,3S)-2-bromo-3-
methylpentane at room temperature?
A)
B)
C)
D)
E) Both A) and C)
Ans: D
155
53. Rearrangements are likely to occur in which of the following reaction types?
A) SN1 reactions
B) SN2 reactions
C) E1 reactions
D) E2 reactions
E) Both SN1 and E1 reactions
Ans: E
54. What is the major product of the reaction of the following reaction?
A)
B)
C)
D)
E) More than one of the above
Ans: A
156
Topic: Alkene Synthesis
Section: 6.10, 6.17, 7.8
Difficulty Level: Easy
A)
B)
C)
D)
E) More than one of the above
Ans: E
157
56. What is the major product for the following reaction?
A)
B)
C)
D)
E) None of the above
Ans: C
A)
B)
C)
D)
E)
Ans: D
158
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 6.17, 7.8
Difficulty Level: Hard
58. What is the major product of the reaction of the following reaction?
A)
B)
C)
D)
E)
Ans: D
159
Section: 6.10, 6.17, 7.8
Difficulty Level: Hard
59. What is the major product of the reaction of the following reaction?
A)
B)
C)
D)
E) None of the above
Ans: A
60. What is the major product of the reaction of the following reaction?
A)
B)
C)
D)
E)
Ans: E
160
Topic: Carbocation Stability, Rearrangement
Section: 4.16, 6.10, 6.17, 7.3, 7.8
Difficulty Level: Medium
61. What is the major product of the reaction of the following reaction sequence?
A)
B)
C)
D)
E) A mixture of A) and B)
Ans: C
161
Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements
Section: 7.7, 7.8
Difficulty Level: Medium
62. Which alkene would you expect to be the major product of the following dehydration?
A) I
B) II
C) III
D) IV
E) V
Ans: C
162
63. What will be the major product of the following reaction?
A)
B)
C)
D)
E)
Ans: A
D) All of these
E) Answers B) and C) only
Ans: B
163
Difficulty Level: Easy
66. Which reaction conditions would not yield 2-butyne from 1-propyne?
A)
B)
C)
D)
E) More than one of these
Ans: A
164
67. Which of the following reactions would yield 2-pentyne?
A)
B)
C)
D)
E)
Ans: B
165
Topic: Alkyne Synthesis
Section: 7.11, 7.12
Difficulty Level: Medium
70. Which reaction would not result in alkylation of the acetylide anion?
A)
B)
C)
D)
E) None of the above
Ans: C
71. Which reaction would not primarily proceed via an SN2 mechanism?
A)
B)
C)
D)
E) All of them proceed via SN2
Ans: C
166
72. Which would be the major product of the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: D
74. A compound X with the formula C7H10 undergoes catalytic hydrogenation to produce a
compound Y with the formula C7H14. What could be true of X?
A) X might have one triple bond and one ring.
B) X might have two double bonds and one ring.
C) X might have one double bond and two rings.
D) X might have one double bond and one triple bond.
E) More than one of the above
Ans: E
167
75. A compound, C6H10, which reacts with 2 mol of hydrogen over a platinum catalyst and
which shows an IR absorption band at approximately 3300 cm-1 could be:
A) I
B) II
C) III
D) IV
E) V
Ans: C
76. What is the structure of a compound with formula C6H10 which has IR absorption at
approximately 3300 cm-1 and which can be catalytically reduced with hydrogen to 2-
methylpentane?
A)
B)
C)
D)
E)
Ans: D
168
77. Upon catalytic hydrogenation, a compound C6H6 absorbs four moles of hydrogen.
Select a structure for C6H6.
A) I, II
B) III
C) II, III
D) IV, V
E) I, IV, V
Ans: D
78. Given:
One can conclude that X has:
A) no rings and no double bonds.
B) no rings and one double bond.
C) one ring and one double bond.
D) two rings and no double bonds.
E) one triple bond.
Ans: C
169
79. On hydrogenation, a compound C9H12 absorbs 2 mol of hydrogen. Which of the
following is a possible structure for the compound?
A) I
B) II
C) III
D) IV
E) V
Ans: D
80. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: E
170
81. Which would be the major product of the following reaction sequence?
A) (CH3CH2)2C=C=CHT
B) (CH3CH2)2C=C=CH2
C) (CH3CH2)2CHCCT
D) (CH3CH2)2CHCH=CHT
E) None of the above
Ans: E
82. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: B
83. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: A
171
Topic: Alkene Reactions, Reaction Mechanisms
Section: 4.16, 7.14A
Difficulty Level: Medium
A) I
B) II
C) III
D) IV
E) V
Ans: A
85. Which would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
Ans: C
172
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.7, 7.15
Difficulty Level: Medium
87. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E)
Ans: D
173
Topic: Alkene Synthesis
Section: 7.10A, 7.15
Difficulty Level: Medium
88. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: C
89. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: C
90. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: C
174
Topic: Alkene Synthesis
Section: 7.11, 7.12, 7.15
Difficulty Level: Medium
91. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: C
92. What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: D
93. Which of these is the most satisfactory method for the preparation of cis-2-pentene?
A) CH3CHBrCH2CH2CH3 + (CH3)3COK/(CH3)3COH
B) CH3CCCH2CH3 + H2, Pt
C) CH3CCCH2CH3 + H2, Ni2B (P-2)
D) CH3CCCH2CH3 + Li/liq. NH3
E) CH3CH2CHBrCH2CH3 + CH3CH2ONa/CH3CH2OH
Ans: C
175
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.13, 7.15
Difficulty Level: Easy
176
Topic: Alkyne Synthesis, Catalytic hydrogenation
Section: 7.11, 7.15A
Difficulty Level: Medium
96. The structure of the product, C, of the following sequence of reactions would be:
A)
B)
C)
D)
E)
Ans: A
177
97. Which would be the major product of the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: B
98. Which would be the major product of the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: A
178
Topic: Dissolving Metal Reduction; trans-hydrogenation
Section: 7.15B
Difficulty Level: Easy
99. The structure of the product obtained from 2-butyne and Li/C2H5NH2 is:
A)
B)
C)
D)
E)
Ans: A
179
SHORT ANSWER QUESTIONS
100. When an elimination reaction gives the most stable alkene as the major product, we say
that the elimination follows ________________'s rule.
Ans: Zaitsev
101. When an elimination reaction gives the less substituted alkene as the major product, we
say that the elimination follows ________________'s rule.
Ans: Hofmann
104. Carbocations have three options available for further reaction. These options include
reaction with a nucleophile, loss of a beta proton to give an alkene, and
________________.
Ans: rearrangement
180
Topic: General Information
Section: 7.10
Difficulty Level: Medium
106. In hydrogenation reactions, both hydrogen atoms add to the pi system from the same
face of the molecule. This is an example of a(n) _________ addition.
Ans: syn
181
Topic: Alkyne Reduction
Section: 7.15
Difficulty Level: Medium
112. The ambiguous name dimethylcyclopentene does not clearly distinguish between
several structures.
a) Draw the structures of all constitutional isomers corresponding to this name.
b) Indicate which of these is likely to be the most stable, i.e, have the smallest heat of
combustion, justifying your rationale briefly.
c) Which of these structures represents an achiral molecule?
Ans: a)
182
113. Provide a mechanistic explanation for the formation of the observed products in the
following reaction.
Ans:
114. Propose a two-step synthetic strategy for the synthesis of 2-methylhexane from 5-
methyl-2-hexanol.
Ans:
Step 1:
Acid-catalyzed dehydration of 5-methyl-2-hexanol to yield an isomeric mixture of
5-methyl-1-hexene and 5-methyl-2-hexene
Step 2:
Catalytic hydrogenation of the double bond with H2, Ni to yield the desired 2-
methylhexane
115. What new, more stable, carbocation(s) may be formed when the following
carbocation undergoes spontaneous rearrangement?
Ans:
116. Complete the following reaction sequence, providing a brief rationale for your answer.
Ans:
Reaction with PCl5 would afford a geminal dihalide I, which would undergo 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 atom that is labile in
presence of NaNH2; hence, an extra mole equivalent of the base is required to
ensure complete reaction and convert all of the initially formed III into the sodium
alkynide intermediate, II; this, upon acidification, affords the final alkyne product
III.
183
Topic: Nomenclature, Index of Hydrogen Deficiency, IR Spectroscopy, Catalytic Hydrogenation
Section: 2.16, 7.13
Difficulty Level: Medium
117. The IR spectrum of an unknown substance Q, C9H16, is found to have distinct peaks at
3310 cm-1 and 2140 cm-1. Treatment of Q with excess H2 in presence of Raney Ni
affords nearly quantitative yields of 2,3-dimethylheptane. Propose a reasonable
structure for Q, based on the above information, briefly explaining your rationale. Also
give its IUPAC name.
Ans:
184
Topic: Nomenclature, Multistep Synthesis
Section: 7.11, 7.12, 7.15
Difficulty Level: Medium
119. Complete the following reaction, giving structural details of all intermediates as well as
the final product.
Ans:
185