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Package Title: Solomons Test Bank
Course Title: Solomons 11e
Chapter Number: 7
Question type: Multiple Choice
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
Answer: C
Topic: Nomenclature
Section: 4.3, 4.5, 7.2
Difficulty Level: Easy
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
Answer: C
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
3) Name the following compound:
1
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
Answer: B
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
4) Which structure represents (Z)-4-bromohexa-1,3-diene?
Br
A)
B) Br
C) Br
Br
D)
E) None of these choices.
Answer: C
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
5) Which structure represents (E)-1-bromo-2-methylhex-2-ene?
Br
A)
2
Br
B)
C) Br
Br
D)
E) None of these choices.
Answer: A
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
6) Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?
Cl
A) Cl
Cl Cl
B)
Cl
C) Cl
Cl
D) Cl
E) None of these choices.
Answer: B
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
7) A correct IUPAC name for the following compound is:
3
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 these choices.
Answer: E
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
8) The correct IUPAC name for the following compound is:
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
Answer: B
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
9) Select the structure of 4–ethyl-2,3-dimethyl-2-heptene.
A)
B)
4
C)
D)
E)
Answer: B
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
10) The correct IUPAC name for the following compound is:
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
Answer: A
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Medium
11) Name the following compound:
Br
A) (S,Z)-3-bromo-4-methylhex-2-ene
5
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
Answer: A
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
12) Name the following compound:
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
Answer: E
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
13) Name the following compound:
Ph
A) (S,E)-3-methyl-5-phenyl-3-heptene
B) (S,E)-3-methyl-5-benzyl-3-heptene
B) (R,E)-3-methyl-5-phenyl-3-heptene
C) (S,Z)-3-methyl-5-phenyl-3-heptene
D) (R,Z)-3-methyl-5-phenyl-3-heptene
Answer: A
6
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
14) Name the following compound:
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
Answer: B
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
15) Which structure represents (R,Z)-5-methylhept-2-ene?
A)
B)
C)
D)
E) None of these choices.
Answer: D
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
7
16) Name the following compound:
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
Answer: D
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 4.6, 5.7, 7.2
Difficulty Level: Medium
17) Name the following compound:
OH
A) (Z)-5-methylhex-4-en-2-yn-6-ol
B) (E)-5-methylhex-4-en-2-yn-6-ol
C) (E)-2-methylhex-2-en-4-yn-1-ol
D) (Z)-2-methylhex-2-en-4-yn-1-ol
E) (Z)-1-methylhex-2-en-3-yn-1-ol
Answer: C
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 4.6, 5.7, 7.2
Difficulty Level: Medium
18) Which molecule would have the lowest heat of hydrogenation?
I II III IV V
8
A) I
B) II
C) III
D) IV
E) V
Answer: A
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
19) 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 these substances could effectively be compared using heats of hydrogenation data.
Answer: C
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
20) Which alkene would liberate the most heat per mole when subjected to catalytic
hydrogenation?
A)
B)
C)
D)
E)
Answer: A
9
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
21) Rank the following compounds from lowest to highest heat of hydrogenation:
A) I, II, III, IV
B) IV, III, II, I
C) II, III, IV, I
D) I, IV, III, II
E) none of these choices
Answer: E
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Medium
22) 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.
Answer: D
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Medium
10
23) 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 choices.
Answer: B
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
24) 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
Answer: E
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
25) 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 these choices.
11
E) No reaction.
Answer: A
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
26) What is the major product for the following reaction?
t-BuOH, t-BuOK
Cl
A) Ot-Bu
B)
C)
D)
E)
Answer: E
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
27) What is the major product for the following reaction?
t-BuOH, t-BuOK
I
12
A)
B)
C)
D)
E) None of these choices.
Answer: D
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
28) What is the major product for the following reaction?
EtONa, EtOH
I
heat
A)
B)
C)
13
D)
E) None of these choices.
Answer: A
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
29) What is the major product for the following reaction?
Cl
EtOH, EtONa
heat
A)
B)
C)
D)
E)
Answer: A
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
30) What is the major product for the following reaction?
14
Br
t-BuOK, t-BuOH
A)
B)
C)
D)
E)
Answer: E
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
31) What is the major product for the following reaction?
EtONa, EtOH
Br
heat
A)
B)
15
C)
D)
E) More than one of these choices.
Answer: C
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Medium
32) Dehydrohalogenation of tert-pentyl bromide at higher temperatures 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.
Answer: D
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
33) What is the major product for the following reaction?
EtOH, EtONa
Br
heat
A) OEt
B)
16
C)
D)
E)
Answer: C
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Hard
34) What is the major product for the following reaction?
EtOH, EtONa
Cl
heat
A) OEt
B)
C)
D)
E)
Answer: B
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Hard
35) What is the major product for the following reaction?
17
1. NaI, acetone
2. t-BuOH, t-BuOK
OTs
A)
B)
C)
D)
E)
Answer: D
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Medium
36) What is the major product for the following reaction?
1. NaI, acetone
2. t-BuOH, t-BuOK
Cl
A)
B)
C)
D)
E)
Answer: D
18
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
37) What is the major product for the following reaction?
1. NaI, acetone
2. NaOH, EtOH, heat
Cl
A)
B)
C)
D)
E)
Answer: C
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
38) What is the major product for the following reaction?
1. NaI, acetone
2. EtONa, EtOH, heat
Br
A)
B)
C)
19
D)
E)
Answer: B
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
39) Which compound listed below would you expect to be the major product when 2-bromo-2-
methylbutane is refluxed with KOH/ethanol?
OH
A)
B) O
C)
D)
E)
Answer: D
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 6.5, 6.16, 7.6
Difficulty Level: Medium
40) 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.
20
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 3º > 2º > 1º.
Answer: D
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
41) 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 (KOt-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.
Answer: E
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
42) What is the major product of the reaction,
(CH3)3COK
?
(CH3)3COH
Br heat
A) (CH3)2C=C(CH3)2
B) (CH3)3C–CH=CH2
C) (CH3)2C=CHCH3
D) (CH3)2C=CHCH2CH3
E) None of these choices.
Answer: B
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Easy
21
43) Which compound would be the major product?
Br (CH3)3COK
?
(CH3)3COH
heat
A)
B)
C)
OH
D)
E)
Answer: E
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Easy
44) What are the major product(s) formed when cis-1-bromo-2-methylcyclohexane reacts with
sodium isopropoxide in isopropanol?
A) I
B) II
C) I and II
D) III
E) III and IV
Answer: C
22
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