Chapter 7

Chapter Seven
MULTIPLE CHOICE QUESTIONS
Topic: Nomenclature
Section: 4.3, 4.5, 7.2
Difficulty Level: Easy
1. The correct IUPAC name for the following compound is:

Br
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
Topic: Nomenclature; Stereochemistry

Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
2. Name the following compound:
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

Section: 4.3, 4.5, 7.2
130
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

Section: 4.3, 4.5, 7.2
4. Which structure represents (Z)-4-bromohexa-1,3-diene?

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

Section: 4.3, 4.5, 7.2
5. Which structure represents (E)-1-bromo-2-methylhex-2-ene?

A)
B)
C)
D)
Ans: A
131
Section: 4.3, 4.5, 7.2
6. Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?

A)
B)
C)
D)
Ans: B
Topic: Nomenclature
Section: 4.5, 7.2
7. A correct IUPAC name for the following compound is:
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
Ans: E
Topic: Nomenclature
Section: 4.5, 7.2
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
9. Select the structure of 4ethyl-2,3-dimethyl-2-heptene.

A)
B)
C)
D)
E)
Ans: B
Topic: Nomenclature
Section: 4.5, 7.2
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

Section: 4.3, 4.5, 5.7, 7.2
133
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

Section: 4.3, 4.5, 5.7, 7.2
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

Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
134
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

Section: 4.3, 4.5, 5.7, 7.2
14. Which structure represents (R,Z)-5-methylhept-2-ene?

A)
B)
C)
D)
Ans: D

Section: 4.3, 4.5, 4.6, 5.7, 7.2
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
Topic: Alkene Stability, Heats of Hydrogenation and Combustion

Section: 7.3
135
16. Which molecule would have the lowest heat of hydrogenation?
A) I
B) II
C) III
D) IV
E) V
Ans: A

Section: 7.3
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

Section: 7.3
136
18. Which alkene would liberate the most heat per mole when subjected to catalytic
hydrogenation?
A)
B)
C)
D)
E)
Ans: A

Section: 7.3
19. Which alkene is most stable?
A) I
B) II
C) III
D) IV
E) V
Ans: A

Section: 7.3
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
Topic: Alkene Synthesis, Reaction Mechanisms

Section: 7.6
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
Topic: Alkene Synthesis

Section: 7.6
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

Section: 7.6
23. What is the major product for the following reaction?
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

Section: 7.6
139
A)
B)
C)
D)
E)
Ans: E

Section: 7.6
A)
B)
C)
D)
E)
None of the above
Ans: D
140
Section: 7.6
A)
B)
C)
D)
Ans: A

Section: 7.6
A)
B)
C)
D)
E)
Ans: A
141
Section: 7.6
A)
B)
C)
D)
E)
Ans: E
142
Section: 7.6
A)
B)
C)
D)
E) More than one of the above
Ans: C
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms

Section: 7.6
30. Dehydrohalogenation of tert-pentyl bromide will produce 2-methyl-1-butene as the

chief product when:
A) CH3COONa is employed as the base.
B) KOH/C2H5OH is employed as the base.
C) CH3CH2ONa/CH3CH2OH is employed as the base.
D) (CH3)3COK/(CH3)3COH is employed as the base.
E) any base is used, as long as the temperature is sufficiently high.
Ans: D
143
Section: 7.6
A)
B)
C)
D)
E)
Ans: C

Section: 7.6
A)
B)
C)
D)
E)
Ans: B
144
Section: 6.5, 7.6
A)
B)
C)
D)
E)
Ans: C
145
Section: 6.5, 7.6
A)
B)
C)
D)
E)
Ans: D

Section: 6.5, 7.6
146
A)
B)
C)
D)
E)
Ans: C

Section: 6.5, 7.6
A)
B)
C)
D)
E)
Ans: B
147
Section: 6.5, 6.16, 7.6
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

Section: 7.6B
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

Section: 7.6C
39. Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is incorrect to

state that:
A) this base is more effective than ethoxide ion, because it (KO-t-Bu) is the more 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 tert-butyl alcohol.
D) it favors E2 reactions over competing SN2 reactions.
E) it will form, predominantly, the more stable alkene.
Ans: E

Section: 7.6C
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

Section: 7.6C
41. Which compound would be the major product?
A)
B)
C)
D)
E)
Ans: E
150
Topic: Carbocation Stability, Rearrangement
Section: 7.7
42. Which statement(s) is/are true of acid-catalyzed alcohol dehydrations?

A) Protonation of the alcohol is a fast step.
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.
D) Loss of a proton by the carbocation is a fast step.
E) All of the above
Ans: E

Section: 7.7
43. Which product(s) would be produced by acid-catalyzed dehydration of 2-methyl-2-

pentanol?
A)
B)
C)
D)
E)
Ans: B
151
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.7
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
Section: 7.7
45. Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is

the rate determining step?
A)
B)
C)
D)
E)
Ans: B

Section: 7.7
46. Which alcohol would be most easily dehydrated?

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

Section: 7.7
153
47. Which alcohol would be most easily dehydrated?
A) I
B) II
C) III
D) IV
E) V
Ans: B
Topic: Carbocation Stability

Section: 7.7
48. Which alcohol would initially produce the most stable carbocation when treated with
concentrated H2SO4?
A)
B)
C)
D)
E)
Ans: A

Section: 6.10, 6.17, 7.7
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
Section: 6.11B, 7.7B
50. Which of the following carbocations would NOT be likely to undergo rearrangement?
A)
B)
C)
D)
E)
Ans: C

Section: 7.8
51. Neopentyl alcohol, (CH3)3CCH2OH, cannot be dehydrated to an alkene without

rearrangement. What is the chief product of dehydration?
A) I
B) II
C) III
D) IV
E) V
Ans: B

Section: 5.12, 6.10, 6.17, 7.8
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

Section: 6.10, 6.17, 7.8
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

Section: 6.10, 6.17, 7.8
54. What is the major product of the reaction of the following reaction?
A)
B)
C)
D)
Ans: A
156
Section: 6.10, 6.17, 7.8
A)
B)
C)
D)
Ans: E

Section: 6.10, 6.17, 7.8
157
A)
B)
C)
D)
Ans: C

Section: 6.10, 6.17, 7.8
A)
B)
C)
D)
E)
Ans: D
158
Section: 6.10, 6.17, 7.8
A)
B)
C)
D)
E)
Ans: D
159
Section: 6.10, 6.17, 7.8
A)
B)
C)
D)
Ans: A

Section: 6.10, 6.17, 7.8
A)
B)
C)
D)
E)
Ans: E
160
Section: 4.16, 6.10, 6.17, 7.3, 7.8
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
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
Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements

Section: 7.7, 7.8
162
63. What will be the major product of the following reaction?
A)
B)
C)
D)
E)
Ans: A
Topic: Alkene Synthesis, Nomenclature

Section: 7.6C, 7.7, 7.10
64. Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable

percentage yield (i.e., greater than 50%)?
A)
B)
C)
D) All of these
E) Answers B) and C) only
Ans: B
Topic: Alkyne Synthesis

Section: 7.11
163
65. Which reaction would yield 2-butyne?

A) CH3CC:Na + CH3Br
B) CH3CH2Br + HCC:Na
C) CH3:Na + HCCCH3
D) More than one of these
E) None of these
Ans: A

Section: 3.6, 7.11, 7.12
66. Which reaction conditions would not yield 2-butyne from 1-propyne?
A)
B)
C)
D)
E) More than one of these
Ans: A

Section: 7.6, 7.7, 7.11, 7.12
164
67. Which of the following reactions would yield 2-pentyne?
A)
B)
C)
D)
E)
Ans: B

Section: 7.10, 7.11, 7.12
68. Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

A)
B)
C)
D) More than one of these
E) None of these
Ans: D

Section: 7.11, 7.12
69. Which statement is/are true about acetylide anions?

A) They do not alkylate with secondary alkyl halides.
B) Primary alkyl halides are best suited for alkylation.
C) In the presence of tertiary alkyl halides, the acetylide anion acts as base to give an
elimination product.
D) Only two of the above are true.
E) All of the statements are true.
Ans: E
165
Section: 7.11, 7.12
70. Which reaction would not result in alkylation of the acetylide anion?
A)
B)
C)
D)
Ans: C

Section: 7.11, 7.12
71. Which reaction would not primarily proceed via an SN2 mechanism?
A)
B)
C)
D)
E) All of them proceed via SN2
Ans: C
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms

Section: 3.16, 7.13
166
72. Which would be the major product of the following reaction sequence?
A)
B)
C)
D)
Ans: D
Topic: Structure Elucidation

Section: 2.16, 4.16, 7.13
73. An unknown compound, B, has the molecular formula C7H12. On catalytic

hydrogenation 1 mol of B absorbs 2 mol of hydrogen and yields 2-methylhexane. B has
significant IR absorption band at about 3300 and 2200 cm-1. Which compound best
represents B?
A) 3-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 5-methyl-1,3-hexadiene
D) 5-methyl-1-hexyne
E) 2-methyl-1,5-hexadiene
Ans: D
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation

Section: 2.16, 4.16, 4.17, 7.13
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.
Ans: E

Section: 2.16, 4.16, 4.17, 7.13
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

Section: 2.16, 4.16, 4.17, 7.13
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

Section: 4.16, 4.17, 7.13
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

Section: 4.16, 4.17, 7.13
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

Section: 4.16, 4.17, 7.13
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

Section: 7.10A, 7.13
80. What is the major product for the following reaction sequence?
A)
B)
C)
D)
Ans: E

Section: 3.16, 7.10A, 7.13
170
A) (CH3CH2)2C=C=CHT
B) (CH3CH2)2C=C=CH2
C) (CH3CH2)2CHCCT
D) (CH3CH2)2CHCH=CHT
Ans: E

Section: 7.11, 7.12, 7.13
A)
B)
C)
D)
Ans: B

Section: 7.11, 7.12, 7.13
A)
B)
C)
D)
Ans: A
171
Topic: Alkene Reactions, Reaction Mechanisms
Section: 4.16, 7.14A
84. Which would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Ans: A

Section: 7.6, 7.14A
A)
B)
C)
D)
E)
Ans: C
172
Section: 7.6, 7.7, 7.15
86. Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?

A) (CH3)2CHCCH3 + conc. H2SO4
B) (CH3)2CHCCH + Li/liq.NH3
C) (CH3)2CHCH2CH2Br + CH3ONa/CH3OH
D) (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH
E) (CH3)2CHCCH + H2/Ni2B (P-2)
Ans: A

Section: 7.10, 7.15
A)
B)
C)
D)
E)
Ans: D
173
Section: 7.10A, 7.15
A)
B)
C)
D)
Ans: C

Section: 7.11, 7.12, 7.15
A)
B)
C)
D)
Ans: C

Section: 7.11, 7.12, 7.15
A)
B)
C)
D)
Ans: C
174
Section: 7.11, 7.12, 7.15
A)
B)
C)
D)
Ans: C

Section: 7.11, 7.12, 7.15
A)
B)
C)
D)
Ans: D

Section: 7.6, 7.7, 7.13, 7.15
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
94. Which reaction would not be a method for preparing 5-methyl-1-hexyne?

A)
B)
C)
D)
E)
Ans: C
Topic: Alkyne Reduction, Nomenclature, Reaction Mechanisms

Section: 7.13, 7.15
95. Which of the following reductions of an alkyne is NOT correct?

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
176
Topic: Alkyne Synthesis, Catalytic hydrogenation
96. The structure of the product, C, of the following sequence of reactions would be:
A)
B)
C)
D)
E)
Ans: A

177
A)
B)
C)
D)
Ans: B

Section: 6.5, 6.16, 7.11, 7.15A
A)
B)
C)
D)
Ans: A
178
Topic: Dissolving Metal Reduction; trans-hydrogenation
Section: 7.15B
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
Topic: General Information

Section: 7.6B
100. When an elimination reaction gives the most stable alkene as the major product, we say
that the elimination follows ________________'s rule.
Ans: Zaitsev

Section: 7.6C
101. When an elimination reaction gives the less substituted alkene as the major product, we
say that the elimination follows ________________'s rule.
Ans: Hofmann

Section: 7.7
102. In a dehydration reaction, the leaving group is _______________.

Ans: a molecule of water

Section: 7.7
103. Dehydration of alcohols requires a __________________ catalyst.

Ans: strong acid

Section: 7.8
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
Section: 7.10
105. Alkynes can be produced from either __________________ or _________________

dihalides.
Ans: vicinal/geminal

Section: 7.14
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
Topic: Alkene Hydrogenation

Section: 7.14
107. How will you prepare cis-1,2-dimethylcyclohexane from 1,2-dimethylcyclohexene?

Ans: Catalytic hydrogenation with H2, Ni (or Pt/Pd)

Section: 7.15
108. Syn hydrogenation of an alkyne will produce a _________ alkene.

Ans: Cis / Z

Section: 7.15
109. Conversion of alkynes to E-alkenes (trans-alkenes) can be accomplished via a

__________________ reaction.
Ans: dissolving metal reduction
181
Topic: Alkyne Reduction
Section: 7.15
110. How will you prepare trans-2-heptene from 2-heptyne?

Ans: Dissolving metal reduction with metallic Na in NH3(l).
Topic: Nomenclature, Stereochemistry

Section: 4.3, 4.5, 5.7, 7.2
111. Draw the structures of all stereoisomers of 2-chloro-4-methyl-3-hexene, clearly showing

all stereochemical details, using appropriate 3-D representations (dash-wedge, etc.) as
relevant.
Ans:
Topic: Alkene Nomenclature, Relative Stability

Section: 4.5, 7.3
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)
b) Structure I is likely to be the most stable, because it is a tetra-substituted

alkene: II, IV and V are tri-substituted; III and VI are di-substituted.
c) Structure I is achiral
Topic: Carbocation Rearrangement, Alkene Synthesis, Dehydration Mechanism

Section: 7.7
182
113. Provide a mechanistic explanation for the formation of the observed products in the
following reaction.
Ans:
Topic: Nomenclature, Multistep Synthesis

Section: 4.16, 7.7
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

Section: 7.8
115. What new, more stable, carbocation(s) may be formed when the following
carbocation undergoes spontaneous rearrangement?
Ans:
Topic: Alkyne Synthesis, Acid-Base reactions

Section: 7.10
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
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:
The Index of Hydrogen deficiency of Q is 2 (compared with C9H20). The IR data

suggests that Q is a terminal alkyne; thus, there must be no rings in its structure.
The catalytic hydrogenation data provides further details of the carbon skeleton.
Due to the specific substitution pattern in this carbon skeleton, there is only one
possible position for a terminal triple bond. Thus, the structure given above is
consistent with all of the given information.
IUPAC Name: 5,6-dimethyl-1-heptyne
184
Topic: Nomenclature, Multistep Synthesis
Section: 7.11, 7.12, 7.15
118. Propose a reasonable synthetic strategy for the synthesis of trans-6-methyl-3-heptene

from 4-methyl-1-pentyne.
Ans:
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 SN2 process.
Step 3:
Add Na(s)/NH3(l) to give the desired trans-alkene by dissolving metal reduction.
Topic: Alkyne Synthesis, Alkyne Hydrogenation

Section: 7.11, 7.12, 7.15A
119. Complete the following reaction, giving structural details of all intermediates as well as
the final product.
Ans:
185

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Chapter 7

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Chapter Seven

MULTIPLE CHOICE QUESTIONS

1. The correct IUPAC name for the following compound is:

Topic: Nomenclature; Stereochemistry

2. Name the following compound:

Topic: Nomenclature; Stereochemistry

3. Name the following compound:

Topic: Nomenclature; Stereochemistry

4. Which structure represents (Z)-4-bromohexa-1,3-diene?

Topic: Nomenclature; Stereochemistry

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

6. Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?

7. A correct IUPAC name for the following compound is:

8. The correct IUPAC name for the following compound is:

9. Select the structure of 4ethyl-2,3-dimethyl-2-heptene.

Topic: Nomenclature; Stereochemistry

Topic: Nomenclature; Stereochemistry

12. Name the following compound:

Topic: Nomenclature; Stereochemistry

Topic: Nomenclature; Stereochemistry

14. Which structure represents (R,Z)-5-methylhept-2-ene?

Topic: Nomenclature; Stereochemistry

15. Name the following compound:

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

16. Which molecule would have the lowest heat of hydrogenation?

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

19. Which alkene is most stable?

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

Topic: Alkene Synthesis, Reaction Mechanisms

Topic: Alkene Synthesis

Topic: Alkene Synthesis

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

Topic: Alkene Synthesis

Topic: Alkene Synthesis

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

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

Topic: Alkene Synthesis

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

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

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

Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms

30. Dehydrohalogenation of tert-pentyl bromide will produce 2-methyl-1-butene as the

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

Topic: Alkene Synthesis

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

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

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

Topic: Alkene Synthesis

Topic: Alkene Synthesis

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

Topic: Alkene Synthesis

Topic: Alkene Synthesis

39. Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is incorrect to

Topic: Alkene Synthesis, Reaction Mechanisms

Topic: Alkene Synthesis, Reaction Mechanisms

41. Which compound would be the major product?

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

Topic: Alkene Synthesis, Reaction Mechanisms

43. Which product(s) would be produced by acid-catalyzed dehydration of 2-methyl-2-

45. Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is

Topic: Alkene Synthesis; Alcohol Dehydration

46. Which alcohol would be most easily dehydrated?

105. Alkynes can be produced from either __ or _