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
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

3) Which of the following is a substitution reaction?

A)
B)
C)
D)

I
II
III
IV

Answer:
A
Difficulty: Medium
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

4)

What is the nucleophile in the following reaction?

A)
B)
C)
D)

I
II
III
IV

Answer:
B
Difficulty: Easy
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

5)

What is the electrophile in the following reaction?

A)
B)
C)
D)

I
II
III
IV

Answer:
A
Difficulty: Easy
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

6)

What is the nucleophile in the following reaction?

A)
B)
C)
D)

I
II
III
IV

Answer:
B
Difficulty: Easy
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

7)

What is the electrophile in the following reaction?

A)
B)
C)
D)

I
II
III
IV

Answer:
A
Difficulty: Easy
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

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
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

9)

For the following reaction, label the nucleophile, electrophile, and leaving group.

Br

Electrophile
Leaving Group
Nucleophile
Answer:
Difficulty: Medium
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1

+ 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
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.2

11)

What is the IUPAC name for the following compound?

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
Section Reference 1: 7.2

12)

What is the IUPAC name for the following compound?

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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2

13)

What is the IUPAC name for the following compound?

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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

14)

What is the IUPAC name for the following compound?

Answer:
1,1-dibromocyclobutane
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

15)

What is the IUPAC name for the following compound?

Answer:
2-bromo-5-fluorohexane
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

16)

What is the IUPAC name for the following compound?

Answer:
(1R, 3S)-3-chloro-1-ethyl-1-methylcyclohexane
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Hard

17)

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

A)
B)
C)
D)

I
II
III
IV

Answer:
A
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Easy

18)

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

A)
B)
C)
D)

I
II
III
IV

Answer:
A
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

20)

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

Cl

Answer:
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

21)

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

Br

Br

Br

OR

Br

Answer:
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

22)

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

Answer:

Learning Objective 1: Alkyl Halides

Section Reference 1: 7.2
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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Easy

26)

Which of the following is a secondary alkyl halide?

A)
B)
C)
D)

1-Bromo-2-methylpropane
2-Bromopropane
1-Bromobutane
2-Bromo-2-methylpropane

Answer:
B
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
Difficulty: Medium

27)

Which of the following is a tertiary alkyl halide?

A)
B)
C)
D)

1-Bromo-2-methylpropane
2-Bromopropane
1-Bromobutane
2-Bromo-2-methylpropane

Answer:
D
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
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
Learning Objective 1: Alkyl Halides
Section Reference 1: 7.2
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
Section Reference 1: 7.3
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
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
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
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
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
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Easy
33)

Provide a curved arrow mechanism for the following reaction

Cl

Na CN

CN

+ Na Cl

Answer:
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Medium

34)
Provide a curved arrow mechanism and predict the product for the following
reaction.

Br

(CH3)3P

Answer:
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Hard

P(CH3)3

35)
Provide a curved arrow mechanism and predict the product for the following
reaction.

O
Cl

+ NaCl

Na

Answer:
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Hard

36)

Provide a curved arrow mechanism for the following reaction.

CN
Br

CN

+ Br

Answer:
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Easy

37)

Provide a curved arrow mechanism for the following reaction.

Answer:
I
+I

Cl

Cl

Learning Objective 1: Possible Mechanisms for Substitution Reactions

Section Reference 1: 7.3
Difficulty: Medium

38)

Provide a curved arrow mechanism for the following reaction.

Answer:
Br

+ Br

SH

SH

Learning Objective 1: Possible Mechanisms for Substitution Reactions

Section Reference 1: 7.3
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
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Easy

42)

Consider the following SN2 reaction,

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 double the rate
It would triple the rate
It would increase four times
It would increase the rate six times
Answer:
C
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Easy

43)

Consider the following SN2 reaction,

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
It would double the rate
It would triple the rate
It would increase four times
It would reduce by half
Answer:
D
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

44)

Consider the following SN2 reaction,

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
It would double the rate
It would triple the rate
It would increase four times
It would reduce by half
Answer:
A
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4

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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Easy

47)

A) I
B) II

Predict the product for the following SN2 reaction.

C) III
D) IV
E) V
Answer:
D
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

48)

A)
B)
C)
D)
E)

Predict the product for the following reaction.

I
II
III
IV
None of these
Answer:
C
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

49)

Predict the product for the following reaction.

A)
B)
C)
D)
E)

I
II
III
IV
None of these
Answer:
D
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

50.

Predict the product for the following reaction.

Answer:
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Hard

51)

Predict the product for the following reaction.

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

N3

Answer:
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Easy

55)

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
I>III>II>IV
IV>III>I>II
Answer:
D
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4

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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium
57)

Draw the potential energy diagram for the following reaction.

A)
B)
C)
D)
E)

I
II
III
IV
V
Answer: A
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
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
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

59)

Draw the transition state for the following reaction.

A)
B)
C)
D)

I
II
III
IV

Answer:
B
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Easy

60.

Draw the transition state for the following reaction.

A)
B)
C)
D)

I
II
III
IV

Answer: B
Learning Objective 1: The SN 2 Mechanism
Section Reference 1: 7.4
Difficulty: Medium

61)

Draw the transition state for the following reaction.

(S)-1-iodo-3-methylpentane +NaSCH3
Answer:

H2C

H3CS

Learning Objective 1: The SN 2 Mechanism

Section Reference 1: 7.4
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
Section Reference 1: 7.5
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
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Medium

64)

Draw the potential energy diagram for the following reaction.

A)
B)
C)
D)

I
II
III
IV

Answer: B
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
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
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
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
Section Reference 1: 7.5
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
Learning Objective 1: The SN1 Mechanism
Section Reference 1: 7.5
Difficulty: Medium

68)

Rank the following compounds from most to least reactive in an SN1 reaction.

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
Section Reference 1: 7.5
Difficulty: Easy

69)

A)
B)
C)
D)
E)

Rank the following compounds from most to least reactive in an SN1 reaction.

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
Section Reference 1: 7.5
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
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
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.
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
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
Learning Objective 1: The SN1 Mechanism

Section Reference 1: 7.5

Difficulty: Medium

73)

A)
B)
C)
D)

Predict the product for the following SN1 reaction.

I
II
III
IV
Answer:
A
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

74)

A) I
B) II
C) III

Predict the product for the following SN1 reaction.

D) IV
Answer:
B
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

75)

A)
B)
C)
D)

Predict the product for the following SN1 reaction.

I
II
III
IV
Answer:
A
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

76)

Predict the product(s) for the following reaction.

SH

HS

Answer:
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Medium

77)

Predict the product(s) for the following reaction.

Cl

Cl

Answer:
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Medium

78)

A)
B)
C)
D)
E)

Predict the product(s) for the following reaction.

Both I & IV
II
III
IV
Both II & III

Answer:
E
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Easy

79)

A)
B)
C)
D)
E)

Predict the major product for the following reaction.

I
II
III
IV
V
Answer:
E
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Medium

80)

Provide a curved arrow mechanism for the following reaction.

Answer:
OH

Br

OH2

Br
+ Br

Br
+ H2O

Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction

Section Reference 1: 7.6
Difficulty: Medium

81)

Provide a curved arrow mechanism for the following reaction.

Answer:

Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction

Section Reference 1: 7.6
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

Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction

Section Reference 1: 7.6
Difficulty: Hard

83)

A) I
B) II
C) III

Predict the major product for the following reaction.

D) Both II & IV
E) Both I & III
Answer:
E
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Easy

84)

A)
B)
C)
D)
E)

Predict the major product for the following reaction.

I
II
Both II & III
Both I & IV
V
Answer:
C
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Medium

85)

Predict the major product for the following reaction.

A)
B)
C)
D)
E)

I
II
Both I & III
Both II & IV
None of these
Answer:
C
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Medium

86)

Provide a curved arrow mechanism for the following reaction.

Answer:

Mechanism

Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction

Section Reference 1: 7.6
Difficulty: Medium
87)
Predict the major product(s) and provide a curved arrow mechanism for the
formation of the product.

OH

HO

Answer:

Mechanism

Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction

Section Reference 1: 7.6
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
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Easy

89)

Which of the following compounds will undergo rearrangement during solvolysis

reaction?
B)
B)
C)
D)
E)

3-iodo-5-methylheptane
3-iodo-2-methylheptane
3-iodo-3-methylheptane
3-iodoheptane
cis-1-iodo-3-methylcyclohexane
Answer:
B
Learning Objective 1: Drawing the Complete Mechanism for an SN1 Reaction
Section Reference 1: 7.6
Difficulty: Medium

90)

A)
B)
C)
D)
E)

Predict the product for the following reaction.

I
II
III
IV
None of these
Answer:
A
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
Difficulty: Easy

91)

A)
B)
C)
D)
E)

Predict the product for the following reaction.

I
II
III
IV
None of these
Answer:
A
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
Difficulty: Easy

92)

A)
B)
C)
D)
E)

Predict the product for the following reaction.

I
II
III
IV
V
Answer:
C
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
Difficulty: Medium

93)

Provide a curved arrow mechanism for the following reaction.

Answer:
OH

OH2

Br

Br

Br + H O
2

Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction

Section Reference 1: 7.7
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

Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction

Section Reference 1: 7.7
Difficulty: Hard

95)

Predict the product for the following reaction.

N
H

OH

Answer:
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
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
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Easy

99)

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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Easy

100)

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:
A
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8

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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

102)

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:
A
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

103)

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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

104)

Which of the following is NOT a nucleophile?

A)
B)
C)
D)
E)

OHNH3
CH3OH
NH4+
All of these

Answer:

Learning Objective 1: Determining which Mechanism Predominates

Section Reference 1: 7.8
Difficulty: Easy

105)

Which of the following is a strong nucleophile?

A)
B)
C)
D)
E)

OHH2O
CH3OH
NH4+
All of these

Answer:
A
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Easy

106)

Which of the following is a weak nucleophile?

A)
B)
C)
D)
E)

OHH2O
CH3ONH3
All of these

Answer:
B
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

111)

Which of the following is an aprotic solvent?

A)
B)
C)

IIIIII

D)
E)

IV
none of these

Answer:
C
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Easy
112)

Which of the following is a protic solvent?

A)
B)
C)
D)
E)

IIIIII
IV
none of these

Answer:
B
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

114)

Predict the product for the following reaction.

A)
B)
C)
D)
E)

I
II
III
IV
I & III

Answer:
C
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Easy

115)

Predict the product for the following reaction.

A)
B)
C)
D)

I
II
III
IV

E)

I & II

Answer:
B
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Medium

116)

Predict the product for the following reaction.

A)
B)
C)
D)
E)

I
II
III
IV
V

Answer:
D
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
Difficulty: Hard

117)

Predict the product for the following reaction.

OCH(CH3)2

CH3
CH3

CH3

OCH(CH3)2
CH3

CH3
CH3
Answer:
Learning Objective 1: Determining which Mechanism Predominates
Section Reference 1: 7.8
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
Section Reference 1: 7.9
Difficulty: Easy

119)

A)
B)
C)
D)

Provide the reagents necessary to carry out the following conversion.

HN3 in water
HN3 in acetonitrile
NaN3 in water
NaN3 in acetonitrile

Answer:
D
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Easy

120)

A)
B)
C)
D)

Provide the reagents necessary to carry out the following conversion.

NaCl in water
NaCl in ether
HCl in water
TsCl/pyridine followed by NaCl
Answer:
C
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Medium
121)

A)
B)
C)
D)

Provide the reagents necessary to carry out the following conversion.

NaOH in water
NaOH in ether
H2O
CH3OH
Answer:
C
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Medium

122)

Provide the reagents necessary to carry out the following conversion.

Answer:
1) NaH 2) CH3CH2I
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Hard

123)

Provide the reagents necessary to carry out the following conversion.

Answer:
1) NaBr2) CH3NH2
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Hard

124)

Provide the reagents necessary to carry out the following conversion.

O
O Na
Answer:
1) TsCl/pyridine2)
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Hard

125)

Provide the reagents necessary to carry out the following conversion.

Answer:
CH3CH2OH
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Medium