Organic Chemistry 7th Edition Bruice Test Bank 1

Test Bank for Organic Chemistry 7th Edition
Bruice 0321803221 9781269406772

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0321803221-9781269406772/
Organic Chemistry, 7e (Bruice)
Chapter 6 Reactions of Alkenes
1) Complete the following reaction and provide a detailed, step-by-step mechanism for the
process.
Answer:
Section: 6-1
2) Draw the product.
Answer:
Section: 6-1
3) Provide the structure of the major organic product in the reaction below.
Answer:
1
Copyright © 2014 Pearson Education, Inc.
Section: 6-1
2
Answer:
Section: 6-1
5) Which of the following is the most stable carbocation?
A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 6-2
3
6) Which of the following alkenes reacts with HCl at the slowest rate?
A)
B)
C)
D)
E)
Answer: A
Section: 6-2
7) What is hyperconjugation, and how does it affect carbocation stability?

Answer: Delocalization of electrons by the overlap of a σ bond with an empty p orbital is
hyperconjugation. This effect occurs only when the interacting orbitals are properly aligned. The
more alkyl groups which are substituents of a cationic carbon, the more the cation can be
stabilized by the delocalizing hyperconjugation effects.
Section: 6-2
4
8) Identify the most stable carbocation.
A)
B)
C)
D)
E)
Answer: C
Section: 6-2
5
9) Which alkene reacts the fastest with HBr?
A)
B)
C)
D)
E)
Answer: E
Section: 6-2
10) According to the Hammond Postulate, which of the following is correct?

A) The transition state of an endothermic reaction step will be more reactant-like than product-
like.
B) The intermediate of an endothermic reaction step will be more reactant-like than product-like.
C) The transition state of an exothermic reaction step will be more reactant-like than product-
like.
D) All transition states are more product-like than reactant-like.
E) All transition states are more reactant-like than product-like.
Answer: C
Section: 6-3
6
11) Which of the following compounds will react most rapidly with HCl?
A) 5-methyl-1-hexene
B) 4-methyl-1-hexene
C) (E)-5-methyl-2-hexene
D) (E)-2-methyl-3-hexene
E) 2-methyl-2-hexene
Answer: E
Section: 6-3
12) For an endergonic reaction step, the Hammond postulate allows one to say that ________.
A) the transition state of the step resembles the reactants of the step
B) the transition state of the step resembles the products of the step
C) the step is rate-determining since it has the smallest Ea
D) the reaction containing this step is overall first order
E) the transition state is precisely symmetric with bond-breaking and bond-forming occurring to
the same extent
Answer: B
Section: 6-3
13) Based on the relative stabilities of the intermediates involved, explain the basis for
Markovnikov's rule in the addition of hydrogen halides to alkenes.
Answer: The rate-determining step in this reaction is the production of a carbocation
intermediate. Since this step is endothermic, Hammond's postulate allows one to gauge the
relative stabilities of the transition states by comparing the relative stabilities of the carbocation
intermediates. The reaction pathway which produces the more substituted carbocation will thus
occur more rapidly.
Section: 6-3
14) Which statement(s) are true according to the Hammond postulate?

A) In an exergonic reaction, the transition state is more similar in energy to the reactant than the
product.
B) In an exergonic reaction, the transition state is more similar in energy to the product than the
reactant.
C) In an endergonic reaction, the transition state is more similar in energy to the reactant than the
product.
D) In an endergonic reaction, the transition state is more similar in energy to the product than the
reactant.
E) A and D
F) B and C
Answer: E
Section: 6-3
7
15) Draw the major organic product generated in the reaction below.
Answer:
Section: 6-4
Answer:
Section: 6-4
Answer:
Section: 6-4
Answer:
Section: 6-4
8
Answer:
Section: 6-4
Answer:
Section: 6-4
21) Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-
methylcyclopentane as the major organic product.
Answer:
Section: 6-4
22) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-

methylcyclohexene? Explain.
Answer: Addition to methylenecyclohexane is more highly regioselective. There is a greater
difference in the activation energies leading to a primary and tertiary carbocation than in the
activation energies leading to a secondary and tertiary carbocation.
Section: 6-4
9
23) Provide the major organic product(s) in the reaction below.
Answer:
Section: 6-4
24) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Answer: C
Section: 6-5
25) What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
A) 2-methylpentane
B) 2-methyl-1-pentanol
C) 2-methyl-2-pentanol
D) 2-methyl-3-pentanol
E) 1-methoxypentane
Answer: C
Section: 6-5
10
Answer:
Section: 6-5
Answer:
Section: 6-5
Answer:
Section: 6-5
11
process.
Answer:
Section: 6-5
30) Provide the structure of the major organic product of the following reaction.
Answer:
Section: 6-5
31) Identify the true statements in the mechanism in the addition of water to an alkene.
A) The addition of the electrophile is a slow step.
B) The addition of the nucleophile is a fast step.
C) A carbocation is formed as an intermediate.
D) Water abstracts the extra proton from the protonated alcohol.
E) All of the above
Answer: E
Section: 6-5
Answer:
Section: 6-5
12
Answer:
Section: 6-5
Answer:
Section: 6-6
35) Give the product for the reaction of 1-butene with methanol in the presence of acid.
A) 1-ethoxybutane
B) 2-ethoxybutane
C) 1-methoxybutane
D) 2-methoxybutane
E) 1-butanol
Answer: D
Section: 6-6
Answer:
Section: 6-6
13
Answer:
Section: 6-6
38) Propose a mechanism for the following reaction:
Answer:
Section: 6-7
14
Answer:
Section: 6-7
40) Which of the following alkenes yield(s) 3-bromo-3-methylpentane as the major product upon
addition of HBr?
A) I and II only
B) III only
C) I, II, nad III only
D) all of them
E) none of them
Answer: D
Section: 6-7
41) Which of the following carbocations is likely to rearrange?
A) I
B) II
C) III
D) IV
E) II and IV
Answer: E
Section: 6-7
15
42) What is the name of the major organic product of the following reaction?
A) 3,3-dimethyl-1-butanol
B) 3,3-dimethyl-2-butanol
C) 2,3-dimethyl-2-butanol
D) 2,3-dimethyl-1-butanol
E) 4-methyl-2-pentanol
Answer: C
Section: 6-7
Answer:
Section: 6-7
16
44) Give the major organic product of the reaction shown.
A)
B)
C)
D)
E)
Answer: C
Section: 6-7
45) Which of the following is the best reaction sequence to use if one wants to accomplish a
Markovnikov addition of water to an alkene with minimal skeletal rearrangement?
A) water + dilute acid
B) water + concentrated acid
C) oxymercuration-demercuration
D) hydroboration-oxidation
E) none of the above
Answer: C
Section: 6-8
17
Answer:
Section: 6-8
Answer:
Section: 6-8
Answer:
Section: 6-8
18
Answer:
Section: 6-8
Answer:
Section: 6-8
Answer:
Section: 6-8
19
52) Which statement is true in the oxymercuration-reduction of an alkene?
A) Markovnikov orientation and syn addition occur.
B) Markovnikov orientation and anti addition occur.
C) Anti-Markovnikov orientation and syn addition occur.
D) Anti-Markovnikov orientation and anti addition occur.
E) Markonikov orientation and both syn and anti addition occur.
Answer: B
Section: 6-8
53) Give the best product for the following reaction.
A)
B)
C)
D)
E)
Answer: B
Section: 6-8
20
Answer:
Section: 6-8
Answer:
Section: 6-8
Answer:
Section: 6-8
57) Which statement is true in the hydroboration-oxidation of an alkene?

A) Markovnikov orientation and syn addition occur.
B) Markovnikov orientation and anti addition occur.
C) Anti-Markovnikov orientation and syn addition occur.
D) Anti-Markovnikov orientation and anti addition occur.
E) Markovnikov orientation and both syn and anti addition occur.
Answer: C
Section: 6-9
21
58) Provide the major organic product in the reaction below.
A)
B)
C)
D)
E)
Answer: A
Section: 6-9
22
59) What reagents are needed to accomplish the following transformation?
A) H2O/H+
B) H2O/Peroxide
C) OH-
D) BH3
E) 1. BH3/ 2. HO-, H2O2, H2O
Answer: E
Section: 6-9
60) What reagents can best be used to accomplish the following transformation?
A) 1. BH3∙THF 2. HO-, H2O2

B) H+, H2O
C) 1. Hg(OAc)2, H2O/THF 2. NaBH4
D) 1. Hg(O2CCF3)2, CH3OH 2. NaBH4
E) NaOH, H2O
Answer: A
Section: 6-9
Answer:
Section: 6-9
23
Answer:
Section: 6-9
Answer:
Section: 6-9
Answer:
Section: 6-9
24
65) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 6-10
25
66) Which reaction intermediate is formed when Br2/CCl4 reacts with cyclohexene?
A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 6-10
Answer:
Section: 6-10
Answer:
Section: 6-10
26
process.
Answer:
(plus enantiomer)
Section: 6-10
70) Provide a detailed, step-by-step mechanism for the reaction shown below.
Answer:
Section: 6-10
71) Draw the structure of the major product of the reaction below.
Answer:
Section: 6-10
27
Answer:
Section: 6-10
Answer:
Section: 6-10
74) Give the product for the reaction that occurs when 1-pentene is treated with Cl2.
A) 1-chloropentane
B) 2-chloropentane
C) 1,1-dichloropentane
D) 2,2-dichloropentane
E) 1,2-dichloropentane
Answer: E
Section: 6-10
75) Give the intermediate for the halohydrin reaction.

A) a halonium ion
B) the most stable carbocation with OH on the adjacent carbon
C) the most stable carbocation with X on the adjacent carbon
D) a cyclic oxonium ion
E) the most stable carbanion
Answer: A
Section: 6-10
28
76) Provide the major organic product in the reaction below.
A)
B)
C)
D)
E)
Answer: A
Section: 6-10
29
Answer:
Section: 6-10
Answer:
Section: 6-10
Answer:
Section: 6-10
30
80) Draw the products.
Answer:
Section: 6-11
Answer:
Section: 6-11
82) Which of the following reagents gives the reaction shown below?
CH3CH= CH2 + ? → CH3CH2CH3
A) H2/HCl
B) H2/H2SO4
C) H2/Ni
D) H2O/Ni
E) H2O/H2SO4
Answer: C
Section: 6-13
31
Answer:
Section: 6-13
84) What is the product of the hydrogenation of an alkene?

A) dihaloalkane
B) alkane
C) haloalkane
D) alcohol
E) ether
Answer: B
Section: 6-13
Answer:
Section: 6-13
32
86) Which of the following is the most stable alkene?
A)
B)
C)
D)
E)
Answer: E
Section: 6-14
87) Upon hydrogenation, which of the following alkenes releases the least heat per mole?
A) 3,4-dimethyl-1-hexene
B) (Z)-3,4-dimethyl-2-hexene
C) (E)-3,4-dimethyl-2-hexene
D) (Z)-3,4-dimethyl-3-hexene
E) (E)-3,4-dimethyl-3-hexene
Answer: E
Section: 6-14
88) Which of the following alkenes would have the smaller heat of hydrogenation? Explain.
CH2 CH2 or CH3CH CH2
Answer: CH3CH CH2 would have the smaller heat of hydrogenation because the double bond
is more stable than that of The greater stability is due to the fact that the double bond
in propene is more alkyl substituted than that of ethene.
Section: 6-14
33
89) What configurations are found in the product(s) of the reaction below?
A) 1R,2R only
B) 1S,2S only
C) 1R,2S only
D) an equal mixture of 1R,2R and 1S,2S
E) an equal mixture of 1R,2R and 1R,2S
Answer: D
Section: 6-16
90) Provide the structure of the major organic product of each of the following reactions.
Answer:
Section: 6-16
91) Identify the products of cis-3-methyl-3-hexene with hydrogen bromide.

A) (2R, 3S)-3-bromo-3-methylhexane
B) (2R, 3R)-3-bromo-3-methylhexane
C) (2S, 3R)-3-bromo-3-methylhexane
D) (2S, 3S)-3-bromo-3-methylhexane
E) All of the above answers
Answer: E
Section: 6-16
34
92) Give the types of products formed from the bromination and catalytic hydrogenation (using
D2) of cyclohexene.
Answer: Threo or trans isomers from bromination; Erythro or cis isomers from hydrogenation.
Section: 6-16
93) Complete the following tree of reactions by giving the major products:
Answer:
Section: 6-19
35

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Organic Chemistry 7th Edition Bruice Test Bank 1

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Test Bank for Organic Chemistry 7th Edition

Bruice 0321803221 9781269406772

2) Draw the product.

5) Which of the following is the most stable carbocation?

7) What is hyperconjugation, and how does it affect carbocation stability?

10) According to the Hammond Postulate, which of the following is correct?

14) Which statement(s) are true according to the Hammond postulate?

22) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-

24) What is the major product of the following reaction?

36) Draw the product.

38) Propose a mechanism for the following reaction:

41) Which of the following carbocations is likely to rearrange?

43) Provide the major organic product(s) in the reaction below.

51) Provide the major organic product(s) in the reaction below.

53) Give the best product for the following reaction.

57) Which statement is true in the hydroboration-oxidation of an alkene?

A) 1. BH3∙THF 2. HO-, H2O2

63) Provide the major organic product(s) in the reaction below.

73) Provide the major organic product(s) in the reaction below.

75) Give the intermediate for the halohydrin reaction.

78) Draw the product.

CH3CH= CH2 + ? → CH3CH2CH3

84) What is the product of the hydrogenation of an alkene?

91) Identify the products of cis-3-methyl-3-hexene with hydrogen bromide.

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