CH 07

Package Title: Test Bank
Course Title: Klein 2e

Chapter Number: 7
Question type: Multiple Choice
1)
Which of the following is a substitution reaction?
A) I
B) II
C) III
D) IV
Answer:
B
Difficulty: Easy
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1
2) Which of the following is a substitution reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
C
Difficulty: Easy
3) Which of the following is a substitution reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Medium
4)
What is the nucleophile in the following reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
B
Difficulty: Easy
5)
What is the electrophile in the following reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
6)
What is the nucleophile in the following reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
B
Difficulty: Easy
7)
What is the electrophile in the following reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
8)
For the following reaction, label the nucleophile, electrophile, and leaving group.
leaving group
Br
SCH3
Answer:
electrophile
Na SCH3
Na Br
nucleophile
Difficulty: Medium
9)
For the following reaction, label the nucleophile, electrophile, and leaving group.
Br
Electrophile
Leaving Group
Nucleophile
Answer:
Difficulty: Medium
+ Br
10)
What is the IUPAC name for the following compound?
A)
B)
C)
D)
3-Fluorobutane
2-Fluorobutane
(S)-2-Fluorobutane
(R)-2-Fluorobutane
Answer:
C
Difficulty: Easy
11)
A)
B)
C)
D)
Chlorocyclopentane
2-Chloro-1-methylcyclopentane
1-Methyl-2-chlorocyclopentane
1-Chloro-2-methylcyclopentane
Answer:
D
Difficulty: Easy
Learning Objective 1: Alkyl Halides
12)
A)
B)
C)
D)
E)
2-Bromo-4-pentylhexane
(2S,4S)-2-Bromo-4,5-diethylheptane
3,4-Diethyl-6-bromoheptane
2-Bromo-4-methylhexane
(2R,4R)-2-Bromo-4,5-diethylheptane
Answer:
B
Difficulty: Medium
13)
A)
B)
C)
D)
E)
1,2-bromocyclopentane
(1R, 2S)-1,2-dibromocyclopentane
(1S, 2S)-1,2-dibromocyclopentane
(1S, 2R)-1,2-dibromocyclopentane
(1R, 2R)-1,2-dibromocyclopentane
Answer:
C
Difficulty: Medium
14)
Answer:
1,1-dibromocyclobutane
Difficulty: Medium
15)
Answer:
2-bromo-5-fluorohexane
Difficulty: Medium
16)
Answer:
(1R, 3S)-3-chloro-1-ethyl-1-methylcyclohexane
Difficulty: Hard
17)
What is the correct structure for 2-bromo-3-methylbutane?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
18)
What is the correct structure for 3-ethyl-1-iodocyclohexane?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
19)
What is the correct structure for (2S,5R)-2-fluoro-5-methylnonane?
A)
B)
C)
D)
I
II
III
IV
Answer:
D
Difficulty: Medium
20)
Provide the structure for 1-chloro-4-isopropylheptane.

Cl
Answer:
Difficulty: Medium
21)
Provide the structure for cis-1,2-dibromocyclopentane.
Br
Br
Br
OR
Br
Answer:
Difficulty: Medium
22)
Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.
Answer:

Difficulty: Hard
23)
Which of the following is a primary alkyl halide?
A)
B)
C)
D)
(CH3)2CHCH2Cl
(CH3)2CClCH2CH3
(CH3)2CHCHClCH3
(CH3)2CHCH2CCl(CH3)2
Answer:
A
Difficulty: Easy
24)
Which of the following is a secondary alkyl halide?
A)
B)
C)
D)
(CH3)2CHCH2Cl
(CH3)2CClCH3
(CH3)2CHCHClCH3
(CH3)2CHCH2CCl(CH3)2
Answer:
C
Difficulty: Easy
25)
Which of the following is a tertiary alkyl halide?
A)
B)
C)
D)
(CH3)2CHCH2Cl
(CH3)2CClCH2CH3
(CH3)2CHCHClCH3
(CH3)2CHCH2CHClCH2CH3
Answer:
B
Difficulty: Easy
26)
Which of the following is a secondary alkyl halide?
A)
B)
C)
D)
1-Bromo-2-methylpropane
2-Bromopropane
1-Bromobutane
Answer:
B
Difficulty: Medium
27)
Which of the following is a tertiary alkyl halide?
A)
B)
C)
D)
2-Bromopropane
1-Bromobutane
Answer:
D
Difficulty: Medium
28)
What is the classification for the following halide?
A)
B)
C)
D)
primary halide
secondary halide
tertiary halide
quaternary halide
Answer:
C
Difficulty: Medium
29) Which of the following is a reasonable definition of a concerted reaction?
A) it is a reaction in which bond breaking occurs first
B) it is a reaction in which all bond-breaking and bond-forming occurs at the same time
C) it is a reaction in which bond forming occurs first
D) it is a substitution reaction
Answer:
B
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Difficulty: Easy
30)
A)
B)
C)
D)
When drawing a curved arrow mechanism, the tail of the arrow starts at______.
the bond that is being formed

the atom with the positive charge
the source of electrons that is being moved
the location to which the electrons are being moved
Answer: C
Difficulty: Easy
31)
A)
B)
C)
D)
When drawing a curved arrow mechanism, the head of the arrow goes to____.
the bond that is being formed

the bond that is being broken
the source of electrons that is being moved
the location to which the electrons are being moved
Answer:
D
Difficulty: Easy
32)
A)
B)
C)
D)
I
II
III
IV
Which of the following is not a possible step in a substitution reaction?
Answer: D
Difficulty: Easy
33)
Provide a curved arrow mechanism for the following reaction
Cl
Na CN
CN
+ Na Cl
Answer:
Difficulty: Medium
34)
Provide a curved arrow mechanism and predict the product for the following
reaction.
Br
(CH3)3P
Answer:
Difficulty: Hard
P(CH3)3
35)
Provide a curved arrow mechanism and predict the product for the following
reaction.
O
Cl
+ NaCl
Na
Answer:
Difficulty: Hard
36)
Provide a curved arrow mechanism for the following reaction.
CN
Br
CN
+ Br
Answer:
Difficulty: Easy
37)
Answer:
I
+I
Cl
Cl

Difficulty: Medium
38)
Answer:
Br
+ Br
SH
SH

Difficulty: Medium
39)
A)
B)
C)
D)
E)
Which of the following is the rate equation for the following SN2 reaction?
Rate = k[1-bromopropane]
Rate = k[NaCN]
Rate = k[1-bromopropane] [NaCN]
Rate = k[1-bromopropane]2
Rate = k[1-bromopropane]2 [NaCN]2
Answer:
C
Learning Objective 1: The SN 2 Mechanism
Difficulty: Easy
40)
Which of the following is the rate equation for the following reaction?
CH3CH2CH2CHBrCH3 + NaN3
CH3CH2CH2CHN3CH3 + NaBr
A) Rate = k[CH3CH2CH2CHBrCH3]
B) Rate = k[NaN3]
C)
Rate = k[CH3CH2CH2CHBrCH3] [NaBr]
D) Rate = k[CH3CH2CH2CHBrCH3] [NaN3]
E) Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]
Answer:
D
Difficulty: Medium
41)
Consider the following SN2 reaction,
Assuming no other changes, what is the effect on the rate, if the concentration of 1chloro-3-methylbutane is doubled?
A)
B)
C)
D)
E)
No effect
It would double the rate
It would triple the rate
It would increase four times
It would reduce by half
Answer:
B
Difficulty: Easy
42)
Assuming no other changes, what is the effect on the rate, if the concentration of NaN3 is
tripled?
A)
B)
C)
D)
E)
No effect
It would increase the rate six times
Answer:
C
Difficulty: Easy
43)
Assuming no other changes, what is the effect on the rate, if the concentration of both
1-chloro-3-methylbutane and NaN3 is doubled?
A)
B)
C)
D)
E)
No effect
Answer:
D
Difficulty: Medium
44)
Assuming no other changes, what is the effect on the rate, if the concentration of
2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?
A)
B)
C)
D)
E)
No effect
Answer:
A
Difficulty: Medium
45) Which of the following is a mechanism for an SN2 reaction?
A)
B)
C)
D)
E)
I
II
III
IV
Both I & II
Answer:
C
Difficulty: Easy
46)
A)
B)
C)
D)
E)
Predict the product for the following SN2 reaction.
I
II
III
IV
Both I & II
Answer:
B
Difficulty: Easy
47)
A) I
B) II
C) III
D) IV
E) V
Answer:
D
Difficulty: Medium
48)
A)
B)
C)
D)
E)
Predict the product for the following reaction.
I
II
III
IV
None of these
Answer:
C
Difficulty: Medium
49)
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Answer:
D
Difficulty: Medium
50.
Answer:
Difficulty: Hard
51)
(1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3
N3
Answer:
Difficulty: Hard
52)
A)
B)
C)
D)
E)
Which of the following alkyl halides will undergo the fastest SN2 reaction?
I
II
III
IV
V
Answer:
A
Difficulty: Easy
53)
A)
B)
C)
D)
E)
I
II
III
IV
V
Which of the following alkyl halides is essentially unreactive in an SN2 reaction?
Answer:
B
Difficulty: Medium
54)
A)
B)
C)
D)
E)
Rank the following compounds from most to least reactive in an SN2 reaction.
I>IV>II>III
II>I>IV>III
III>IV>I>II
IV>I>II>III
IV>III>I>II
Answer:
B
Difficulty: Easy
55)
A)
B)
C)
D)
E)
I>IV>II>III
II>I>IV>III
III>IV>I>II
I>III>II>IV
IV>III>I>II
Answer:
D
Difficulty: Medium
56)
A)
B)
C)
D)
E)
Which of the following alkyl halides will undergo the slowest SN2 reaction?
I
II
III
IV
V
Answer:
D
Difficulty: Medium
57)
Draw the potential energy diagram for the following reaction.
A)
B)
C)
D)
E)
I
II
III
IV
V
Answer: A
Difficulty: Medium
58)
Which of the following potential energy diagram represent an exothermic
concerted reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Medium
59)
Draw the transition state for the following reaction.
A)
B)
C)
D)
I
II
III
IV
Answer:
B
Difficulty: Easy
60.
A)
B)
C)
D)
I
II
III
IV
Answer: B
Difficulty: Medium
61)
(S)-1-iodo-3-methylpentane +NaSCH3
Answer:
H2C
H3CS

Difficulty: Hard
62)
A)
B)
C)
D)
Which of the following is the rate equation for the following SN1 reaction?
Rate = k[H2O]
Rate = k[1-chloro-1-methylcyclohexane] [H2O]
Rate = k[chloride ion]
Rate = k[1-chloro-1-methylcyclohexane]
Answer:
D
Learning Objective 1: The SN1Mechanism
Difficulty: Easy
63)
Which of the following is the rate equation for the following reaction?
2-chloro-2-methylpentane + NaI
A)
B)
C)
D)
Rate = k[NaI]
Rate = k[2-chloro-2-methylpentane] [NaI]
Rate = k[chloride ion]
Rate = k[2-chloro-2-methylpentane]
Answer:
D
Difficulty: Medium
64)
Draw the potential energy diagram for the following reaction.
A)
B)
C)
D)
I
II
III
IV
Answer: B
Difficulty: Medium
65)
Which of the following potential energy diagram represent an exothermic SN1
reaction?
A)
B)
C)
D)
I
II
III
IV
Answer:
B
Difficulty: Medium
66)
A)
B)
C)
D)
E)
Which of the following alkyl halides will undergo the fastest SN1 reaction?
I
II
III
IV
V
Answer:
E
Learning Objective 1: The SN1 Mechanism
Difficulty: Easy
67)
A)
B)
C)
D)
E)
Which of the following alkyl halides will undergo the slowest SN1 reaction?
I
II
III
IV
V
Answer:
C
Difficulty: Medium
68)
A)
B)
C)
D)
E)
I>IV>II>III
II>I>IV>III
III>IV>I>II
IV>I>II>III
IV>III>I>II
Answer:
D
Learning Objective 1: The SN 1Mechanism
Difficulty: Easy
69)
A)
B)
C)
D)
E)
I>IV>II>III
II>III>I>IV
III>II>I>IV
I>III>II>IV
IV>III>I>II
Answer:
C
Learning Objective 1: The SN 1Mechanism
Difficulty: Medium
70)
Which of the following compounds will undergo the fastest SN1 reaction?
A)
B)
C)
D)
E)
I
II
III
IV
Both I & IV
Answer:
D
Difficulty: Hard
71)
Which of the following compounds will undergo the fastest SN1 reaction? Explain
your choice.
Answer:
Compound IV The carbocation formed is resonance stabilized with an
octet on all atoms.
Difficulty: Hard
72)
A)
B)
C)
D)
E)
Which of the following is true about the stereochemistry of SN1 reaction?
retention of configuration at the electrophilic center

inversion of configuration at the electrophilic center
50:50 mixture of retention and inversion of configuration at the electrophilic center
slightly more inversion than retention at the electrophilic center
slightly more retention than inversion at the electrophilic center
Answer:
D

Difficulty: Medium
73)
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
74)
A) I
B) II
C) III
D) IV
Answer:
B
Difficulty: Easy
75)
A)
B)
C)
D)
I
II
III
IV
Answer:
A
Difficulty: Easy
76)
Predict the product(s) for the following reaction.
SH
HS
Answer:
Difficulty: Medium
77)
Cl
Cl
Answer:
Difficulty: Medium
78)
A)
B)
C)
D)
E)
Both I & IV
II
III
IV
Both II & III
Answer:
E
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Difficulty: Easy
79)
A)
B)
C)
D)
E)
Predict the major product for the following reaction.
I
II
III
IV
V
Answer:
E
Difficulty: Medium
80)
Answer:
OH
Br
OH2
Br
+ Br
Br
+ H2O

Difficulty: Medium
81)
Answer:

Difficulty: Hard
82)
Predict the major product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
Answer:
Br
Mechanism

Difficulty: Hard
83)
A) I
B) II
C) III
D) Both II & IV
E) Both I & III
Answer:
E
Difficulty: Easy
84)
A)
B)
C)
D)
E)
I
II
Both II & III
Both I & IV
V
Answer:
C
Difficulty: Medium
85)
A)
B)
C)
D)
E)
I
II
Both I & III
Both II & IV
None of these
Answer:
C
Difficulty: Medium
86)
Answer:
Mechanism

Difficulty: Medium
87)
Predict the major product(s) and provide a curved arrow mechanism for the
formation of the product.
OH
HO
Answer:
Mechanism

Difficulty: Hard
88)
A)
B)
C)
D)
E)
I
II
III
IV
V
Which of the following compounds will undergo rearrangement in an SN1 reaction?
Answer: B
Difficulty: Easy
89)
Which of the following compounds will undergo rearrangement during solvolysis

reaction?
B)
B)
C)
D)
E)
3-iodo-5-methylheptane
3-iodoheptane
cis-1-iodo-3-methylcyclohexane
Answer:
B
Difficulty: Medium
90)
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Answer:
A
Difficulty: Easy
91)
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Answer:
A
Difficulty: Easy
92)
A)
B)
C)
D)
E)
I
II
III
IV
V
Answer:
C
Difficulty: Medium
93)
Answer:
OH
OH2
Br
Br
Br + H O
2

Difficulty: Medium
94)
Predict the product and provide a curved arrow mechanism for the formation of the
product.
Answer:
Cl
OH
Cl
OH2
Cl
+ H2O

Difficulty: Hard
95)
N
H
OH
Answer:
Difficulty: Hard
96)
What set of reaction conditions would favor an SN2 reaction on 2-bromo-3methylbutane?

A)
B)
C)
D)
weak nucleophile in a protic solvent

weak nucleophile in an aprotic solvent
strong nucleophile in a protic solvent
strong nucleophile in an aprotic solvent
Answer:
D
Learning Objective 1: Determining which Mechanism Predominates
Difficulty: Easy
97)
What set of reaction conditions would favor an SN1 reaction on 2-bromo-3methylbutane?

A)
B)
C)
D)
weak nucleophile in a protic solvent

weak nucleophile in an aprotic solvent
strong nucleophile in a protic solvent
strong nucleophile in an aprotic solvent
Answer:
A
Difficulty: Easy
98)
What substitution reaction mechanism is most likely for the following compound?
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
C
Difficulty: Easy
99)
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
C
Difficulty: Easy
100)
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
A
Difficulty: Easy
101)
What substitution reaction mechanism is most likely for the following

conversion?
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
B
Difficulty: Medium
102)

conversion?
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
A
Difficulty: Medium
103)

conversion?
A)
B)
C)
D)
SN1
SN2
Either SN1 or SN2
None of these
Answer:
B
Difficulty: Medium
104)
Which of the following is NOT a nucleophile?
A)
B)
C)
D)
E)
OHNH3
CH3OH
NH4+
All of these
Answer:

Difficulty: Easy
105)
Which of the following is a strong nucleophile?
A)
B)
C)
D)
E)
OHH2O
CH3OH
NH4+
All of these
Answer:
A
Difficulty: Easy
106)
Which of the following is a weak nucleophile?
A)
B)
C)
D)
E)
OHH2O
CH3ONH3
All of these
Answer:
B
Difficulty: Easy
107)
Which of the following is a strongest nucleophile in a polar protic solvent?
A)
B)
C)
D)
E)
FClBrIAll of these
Answer:
D
Difficulty: Medium
108)
Which of the following is a weakest nucleophile in a polar protic solvent?
A)
B)
C)
D)
E)
FClBrIAll of these
Answer:
A
Difficulty: Medium
109)
Which of the following is a strongest nucleophile in a polar protic solvent?
A)
B)
C)
D)
E)
FClOHSHAll of these
Answer:
D
Difficulty: Medium
110)
Which of the following compounds has the best leaving group?
A)
B)
C)
D)
E)
I
II
III
IV
All of these
Answer:
D
Difficulty: Medium
111)
Which of the following is an aprotic solvent?
A)
B)
C)
IIIIII
D)
E)
IV
none of these
Answer:
C
Difficulty: Easy
112)
Which of the following is a protic solvent?
A)
B)
C)
D)
E)
IIIIII
IV
none of these
Answer:
B
Difficulty: Easy
113)
Which of the following describes the difference between protic and aprotic
solvents?
A)
B)
C)
D)
E)
protic solvents stabilize anions only

aprotic solvents stabilize anions only
protic solvents stabilize cations only
aprotic solvents stabilize both cations and anions
protic solvents stabilize both cations and anions
Answer:
E
Difficulty: Medium
114)
A)
B)
C)
D)
E)
I
II
III
IV
I & III
Answer:
C
Difficulty: Easy
115)
A)
B)
C)
D)
I
II
III
IV
E)
I & II
Answer:
B
Difficulty: Medium
116)
A)
B)
C)
D)
E)
I
II
III
IV
V
Answer:
D
Difficulty: Hard
117)
OCH(CH3)2
CH3
CH3
CH3
OCH(CH3)2
CH3
CH3
CH3
Answer:
Difficulty: Hard
118)
A)
B)
C)
D)
Provide the reagents necessary to carry out the following conversion.
H2S in water
H2S in DMSO
NaSH in water
NaSH in DMSO
Answer:
D
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Difficulty: Easy
119)
A)
B)
C)
D)
HN3 in water
HN3 in acetonitrile
NaN3 in water
NaN3 in acetonitrile
Answer:
D
Transformation
Difficulty: Easy
120)
A)
B)
C)
D)
NaCl in water
NaCl in ether
HCl in water
TsCl/pyridine followed by NaCl
Answer:
C
Transformation
Difficulty: Medium
121)
A)
B)
C)
D)
NaOH in water
NaOH in ether
H2O
CH3OH
Answer:
C
Transformation
Difficulty: Medium
122)
Answer:
1) NaH 2) CH3CH2I
Transformation
Difficulty: Hard
123)
Answer:
1) NaBr2) CH3NH2
Transformation
Difficulty: Hard
124)
O
O Na
Answer:
1) TsCl/pyridine2)
Transformation
Difficulty: Hard
125)
Answer:
CH3CH2OH
Transformation
Difficulty: Medium

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Package Title: Test Bank

Course Title: Klein 2e

Question type: Multiple Choice

Which of the following is a substitution reaction?

2) Which of the following is a substitution reaction?

3) Which of the following is a substitution reaction?

What is the nucleophile in the following reaction?

What is the electrophile in the following reaction?

What is the nucleophile in the following reaction?

What is the electrophile in the following reaction?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

What is the correct structure for 2-bromo-3-methylbutane?

What is the correct structure for 3-ethyl-1-iodocyclohexane?

What is the correct structure for (2S,5R)-2-fluoro-5-methylnonane?

Provide the structure for 1-chloro-4-isopropylheptane.

Provide the structure for cis-1,2-dibromocyclopentane.

Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.

Learning Objective 1: Alkyl Halides

Which of the following is a primary alkyl halide?

Which of the following is a secondary alkyl halide?

Which of the following is a tertiary alkyl halide?

Which of the following is a secondary alkyl halide?

Which of the following is a tertiary alkyl halide?

What is the classification for the following halide?

the bond that is being formed

the bond that is being formed

Which of the following is not a possible step in a substitution reaction?

Provide a curved arrow mechanism for the following reaction

Provide a curved arrow mechanism for the following reaction.

Provide a curved arrow mechanism for the following reaction.

Learning Objective 1: Possible Mechanisms for Substitution Reactions

Provide a curved arrow mechanism for the following reaction.

Learning Objective 1: Possible Mechanisms for Substitution Reactions

Consider the following SN2 reaction,

Consider the following SN2 reaction,

Consider the following SN2 reaction,

Consider the following SN2 reaction,

45) Which of the following is a mechanism for an SN2 reaction?

Predict the product for the following SN2 reaction.

Predict the product for the following SN2 reaction.

Predict the product for the following reaction.

Predict the product for the following reaction.

Predict the product for the following reaction.

Predict the product for the following reaction.

(1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3

Which of the following alkyl halides is essentially unreactive in an SN2 reaction?

Draw the potential energy diagram for the following reaction.

Draw the transition state for the following reaction.

Draw the transition state for the following reaction.

Draw the transition state for the following reaction.

Learning Objective 1: The SN 2 Mechanism

Draw the potential energy diagram for the following reaction.