CH 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:

OCH3
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
Section: 4.3, 4.5, 7.2
HO
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) Br
B)
Br
C)
Br
D) Br
E) None of the above

Ans: C
131
Section: 4.3, 4.5, 7.2
5. Which structure represents (E)-1-bromo-2-methylhex-2-ene?

A) Br
B) Br
C)
Br
D) Br

Ans: A

Section: 4.3, 4.5, 7.2
6. Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?

A)
Cl
Cl
B) Cl Cl
C) Cl
Cl
D) Cl
Cl
Ans: B
132
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
133
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
Cl
Br
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
134
Section: 4.3, 4.5, 5.7, 7.2

Br
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

Br
Br
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
135
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
OH
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
136
Section: 4.3, 4.5, 4.6, 5.7, 7.2

Cl
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
16. Which molecule would have the lowest heat of hydrogenation?
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A
137
Section: 7.3
17. Heats of hydrogenation data would be useful in comparing the relative stabilities of
which of the following substances?
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

Section: 7.3
18. Which alkene would liberate the most heat per mole when subjected to catalytic
hydrogenation?
A)
B)
C)
D)
E)
Ans: A
138
Section: 7.3
19. Which alkene is most stable?
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

Section: 7.3
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
139
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?
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
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
140
Section: 7.6
23. What is the major product for the following reaction?

EtOH, EtONa
OTs
heat
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

t-BuOH, t-BuOK
Cl
A)
Ot-Bu
B)
C)
D)
E)
Ans: E
141
Section: 7.6
t-BuOH, t-BuOK
I
A)
B)
C)
D)

Ans: D
142
Section: 7.6

EtONa, EtOH
I
heat
A)
B)
C)
D)

Ans: A
143
Section: 7.6

Cl
EtOH, EtONa
heat
A)
B)
C)
D)
E)
Ans: A
144
Section: 7.6

Br
t-BuOK, t-BuOH
A)
B)
C)
D)
E)
Ans: E
145
Section: 7.6

EtONa, EtOH
Br
heat
A)
B)
C)
D)
E) More than one of the above

Ans: C
146
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

Section: 7.6

EtOH, EtONa
Br
heat
A)
OEt
B)
C)
D)
E)
Ans: C
147
Section: 7.6

EtOH, EtONa
Cl
heat
A)
OEt
B)
C)
D)
E)
Ans: B
148
Section: 6.5, 7.6

1. NaI, acetone
2. t-BuOH, t-BuOK
OTs
A)
B)
C)
D)
E)
Ans: C
149
Section: 6.5, 7.6

1. NaI, acetone
2. t-BuOH, t-BuOK
Cl
A)
B)
C)
D)
E)
Ans: D
150
Section: 6.5, 7.6

1. NaI, acetone
2. NaOH, EtOH, heat

Cl
A)
B)
C)
D)
E)
Ans: C
151
Section: 6.5, 7.6

1. NaI, acetone
2. EtONa, EtOH, heat

Br
A)
B)
C)
D)
E)
Ans: B
152
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) OH
B)
O
C)
D)
E)
Ans: D

Section: 7.6B
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
153
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
40. What is the major product of the reaction,

(CH3)3COK
?
(CH3)3COH
Br heat
A) (CH3)2C=C(CH3)2
B) (CH3)3CCH=CH2
C) (CH3)2C=CHCH3
D) (CH3)2C=CHCH2CH3
E) None of these
Ans: B
154
Section: 7.6C
41. Which compound would be the major product?

Br (CH3)3COK
?
(CH3)3COH
heat
A) O
B)
C)
D) OH
E)
Ans: E
155
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)
and
C)
and
D)
E)
O
Ans: B
156
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.7
44. Which one of the following alcohols would dehydrate most rapidly when treated with
sulfuric acid?
OH OH OH
I II III
OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
157
Section: 7.7
45. Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is

the rate determining step?
A) Step 1:
+ H3O+ + H2O
OH OH2
B) Step 2:
+ H2O
OH2
C) Step 3:
D) Step 4a:
+ H2O + H3O+
E) Step 4b:
+ H 2O + H3O+
Ans: B
158
Section: 7.7
46. Which alcohol would be most easily dehydrated?

A) CH3
CH3CH2CCH2CH3
OH
B) CH3
CH3CH2CHCHCH3
OH
C) CH3
CH3CH2CHCH2CH2OH
D) CH3
HOCH2CHCH2CH2CH3
E) CH2OH
CH3CH2CHCH2CH3
Ans: A

Section: 7.7
47. Which alcohol would be most easily dehydrated?
OH OH OH
I II III
OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
159
Topic: Carbocation Stability
Section: 7.7
48. Which alcohol would initially produce the most stable carbocation when treated with
concentrated H2SO4?
A) OH
B)
OH
C)
OH
D)
HO
E) HO
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
160
Section: 6.11B, 7.7B
50. Which of the following carbocations would NOT be likely to undergo rearrangement?
A) CH3CHCHCH3
CH3
B) CH3
CH3CHCCH3
CH3
C) CH3
CH3CCH2CH3
D) CH3
CH3CHCH2
E) CH3
CH3CCHCH2CH3
CH3
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?
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
161
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) OCH3
C)
D)
H3CO
E) Both A) and C)
Ans: D

Section: 6.10, 6.17, 7.8
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
162
Section: 6.10, 6.17, 7.8
54. What is the major product of the reaction of the following reaction?
I
ethanol, 20 oC
A)
CH3CH2O
B) OCH2CH3
C)
D)

Ans: A
163
Section: 6.10, 6.17, 7.8
EtOH, heat
Br
A)
B)
C)
D)

Ans: E
164
Section: 6.10, 6.17, 7.8
EtOH, heat
I
A)
B)
C)
D)

Ans: C
165
Section: 6.10, 6.17, 7.8

Cl
EtOH, heat
A)
B)
C)
D)
E)
Ans: D
166
Section: 6.10, 6.17, 7.8
Cl
EtOH, heat
A)
B)
C) OEt
D)
E)
Ans: D
167
Section: 6.10, 6.17, 7.8
EtOH, heat
OTs
A)
B)
C)
OEt
D)

Ans: A
168
Section: 6.10, 6.17, 7.8
CH3OH, heat
Cl
A)
H3CO
B)
C)
D)
E)
Ans: E
169
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?
Br
1. H2, Ni
2. EtOH, heat
A)
B)
C)
D) OEt
E) A mixture of A) and B)
Ans: C
170
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?
H2SO4
?
heat
OH
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
171
Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements
Section: 7.7, 7.8
63. What will be the major product of the following reaction?

85% H3PO4
?
heat
OH
A)
B)
C)
D) O
E)
Ans: A
172
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) H2SO4
heat
OH
B) (CH3)3COK, (CH3)3COH
heat
Br
C) i) 3 NaNH2, mineral oil, heat
Br
ii) H3O+
Br
D) All of these
E) Answers B) and C) only
Ans: B
Topic: Alkyne Synthesis

Section: 7.11
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
173
Section: 3.6, 7.11, 7.12
66. Which reaction conditions would not yield 2-butyne from 1-propyne?
A) a. EtONa, EtOH
b. CH3I
B) a. CH3Li, THF
b. CH3I
C) a. NaNH2, NH3 (liq)
b. CH3I
D) a. NaCH2CH3, THF
b. CH3I
E) More than one of these
Ans: A

Section: 7.6, 7.7, 7.11, 7.12
67. Which of the following reactions would yield 2-pentyne?

A) NaNH2 I
(1 mol)
B) NaNH2 Br
(1 mol)
C) Br
CH3OH
Br
D) HA
heat
OH
E) Br
NaOC2H5
C2H5OH
Ans: B
174
Section: 7.10, 7.11, 7.12
68. Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

A) CH3
C2H5 C C C: Na H3C I
CH3
B) CH3
H3C C C: Na C2H5 C Br
CH3
C) NaNH2 ( excess)
NH3 (l)
Br Br
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
175
Section: 7.11, 7.12
70. Which reaction would not result in alkylation of the acetylide anion?
A) Br
Li
B) Cl
Li
C)
Br
Li
D)
OTs
Li
Ans: C

Section: 7.11, 7.12
71. Which reaction would not primarily proceed via an SN2 mechanism?
A) Br
Li
B) Cl
Li
C)
Br
Li
D)
OTs
Li
E) All of them proceed via SN2
Ans: C
176
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 3.16, 7.13
72. Which would be the major product of the following reaction sequence?
1a. NaNH2, NH3 (liq.)
1b. T3O+
2. H2, Pd/C
A)
CH2CH3
B)
CH=CHT
C)
CH=CH2
D)
CH2CH2T
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
177
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
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:
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
178
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
77. Upon catalytic hydrogenation, a compound C6H6 absorbs four moles of hydrogen.
Select a structure for C6H6.
I II III IV V
A) I, II
B) III
C) II, III
D) IV, V
E) I, IV, V
Ans: D
179
Section: 4.16, 4.17, 7.13
78. H2, Pt
X (C8H14) Y (C8H16)
Given: 25oC
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
79. On hydrogenation, a compound C9H12 absorbs 2 mol of hydrogen. Which of the

following is a possible structure for the compound?
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
180
Section: 7.10A, 7.13
80. What is the major product for the following reaction sequence?
1a. NaNH2 (excess)
mineral oil, heat
Cl 1b. NH4Cl
Cl
2. H2 (excess), Pd/C
A)
B) C
C)
D)

Ans: E

Section: 3.16, 7.10A, 7.13
1a. NaNH2 (excess)
Cl mineral oil, heat
Cl
1b. T3O+
H
2. H2, Pd/C
A) (CH3CH2)2C=C=CHT
B) (CH3CH2)2C=C=CH2
C) (CH3CH2)2CHCCT
D) (CH3CH2)2CHCH=CHT
Ans: E
181
Section: 7.11, 7.12, 7.13
H 1b. CH3CH2CH2Br
H 2. H2 (excess), Pd/C
A)
B)
C)
D) N
H
Ans: B

Section: 7.11, 7.12, 7.13
1b. CH3CH2CH2Br
2. H2 (excess), Pd/C
A)
B) CH3CH2CH2Br
C)
D)

Ans: A
182
Topic: Alkene Reactions, Reaction Mechanisms
Section: 4.16, 7.14A
84. Which would be the major product of the following reaction?
D2, Ni
?
D D CH3
D CH3 H CH3 DD
H D H
I II III
CH3 D
DH D CH3
D H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A
183
Section: 7.6, 7.14A
1. EtOH, EtONa
2. D2, Pd/C
Br
A)
B)
C)
D
D
H
D)
D
H
D
E)
D
D
Ans: C
184
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
Br
1. NaNH2 (excess)
mineral oil, heat
2. H2, Pd/CaCO3
Br quinoline
A)
B)
C)
D)
E)
Ans: D
185
Section: 7.10A, 7.15
1a. NaNH2 (excess)
mineral oil, heat
Cl 1b. NH4Cl
Cl
2. H2, P-2
A)
B) C
C)
D)

Ans: C

Section: 7.11, 7.12, 7.15
H 1b. CH3CH2CH2Br
H 2a. Li, CH3CH2NH2

2b. NH4Cl
A)
B)
C)
D) N
H
Ans: C
186
Section: 7.11, 7.12, 7.15
H 1b. CH3CH2CH2Br
H 2. H2, Pd/CaCO3
quinoline
A)
B)
C)
D) N
H
Ans: C

Section: 7.11, 7.12, 7.15
1b. CH3CH2CH2Br
2a. Li, CH3CH2NH2

2b. NH4Cl
A)
B) CH3CH2CH2Br
C)
D)

Ans: C
187
Section: 7.11, 7.12, 7.15
1a. n-BuLi, THF
1b. CH3CH2CH2Br
2. H2, P-2
A)
B) CH3CH2CH2Br
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
188
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)
1) NaNH2 (2 mol), liq NH3
Br
2) NH4+
B)
HC CNa + Cl
C)
Li + HC CH
D) 1) NaNH2 (3 mol), liq NH3
Br
2) NH4+
Br
E) Br
1) NaNH2 (3 mol), liq NH3
Br
2) NH4+
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
189
Topic: Alkyne Synthesis, Catalytic hydrogenation
96. The structure of the product, C, of the following sequence of reactions would be:
NaNH2 CH3CH2Br H2
A B C
NH3(l) Ni2B [P-2]
A)
B)
C)
D) Br
E)
Ans: A
190
1. D2, Pd/CaCO3
quinoline
2. H2, Ni
A) D
D
B) D
D
C)
D
D
D)

Ans: B
191
Section: 6.5, 6.16, 7.11, 7.15A
1b. CH2=CHCH2Br
2. D2, P-2
A)
D
D
B)
D D H D
D
H
D D H
C) D
D
D)

Ans: A
192
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)
HN
D)
NH
E)
Ans: A
193
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
194
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)
H2, Ni

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
195
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).
Na, 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: 2-chloro-4-methyl-3-hexene
Cl H H Cl Cl H H Cl
(2R, 3E) (2S, 3E) (2R, 3Z) (2S, 3Z)
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)
dimethylcyclopentene
I II III IV V VI
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
196
Topic: Carbocation Rearrangement, Alkene Synthesis, Dehydration Mechanism
Section: 7.7
113. Provide a mechanistic explanation for the formation of the observed products in the
following reaction.
H3O+
OH
heat
Ans: H
: :
:O H
:
1) OH OH2 :O H
:
H H
rearrangement
2) OH2+
[-H2O]
:
H
3a) :O H
:
:O H
H H H
H
Both
H
H H H
3b) :O H
:
:O H
H H
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: OH
H3O+ H2
+
heat Ni
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
197
Section: 7.8
115. What new, more stable, carbocation(s) may be formed when the following
carbocation undergoes spontaneous rearrangement?
Ans:
via a Methyl (methide) shift via a Hydrogen (hydride) shift
Topic: Alkyne Synthesis, Acid-Base reactions

Section: 7.10
116. Complete the following reaction sequence, providing a brief rationale for your answer.
O
i) PCl5
?
ii) 3 NaNH2,
mineral oil, heat
iii) H3O+
Ans: O Cl Na
Cl
PCl5 3 NaNH2, H3O+
mineral oil, heat
I (-2HCl) II III
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.
198
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: H
excess H2
Ni
IR: 2140, 3310 cm-1 2,3-dimethylheptane
Substance Q: 5,6-
dimethyl-1-heptyne
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
199
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: 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 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.
1) NaNH2, NH3 (l)

?
2) CH3CH2CH2Br
3) H2, Lindlar catalyst
Ans: NaNH2
NH3 (l) Na
:
CH3CH2CH2Br
H2
Lindlar catalyst
200

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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:

3. Name the following compound:

Topic: Nomenclature; Stereochemistry

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

E) None of the above

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

E) None of the above

Topic: Nomenclature; Stereochemistry

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.

11. Name the following compound:

Topic: Nomenclature; Stereochemistry

12. Name the following compound:

13. Name the following compound:

Topic: Nomenclature; Stereochemistry

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

E) None of the above

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

19. Which alkene is most stable?

Topic: Alkene Stability, Heats of Hydrogenation and Combustion

20. Concerning the relative stabilities of alkenes, which is a false statement?

Topic: Alkene Synthesis

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

Topic: Alkene Synthesis

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

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

E) None of the above

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

E) None of the above

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?

E) More than one of the above

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

Topic: Alkene Synthesis

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

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?

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

2. NaOH, EtOH, heat

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

2. EtONa, EtOH, heat

Topic: Alkene Synthesis

38. Zaitsev's rule states that:

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

Topic: Alkene Synthesis, Reaction Mechanisms

40. What is the major product of the reaction,

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

46. Which alcohol would be most easily dehydrated?

105. Alkynes can be produced from either __ or _