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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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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

+ Na SCH3 + Na Br

electrophile nucleophile
Answer:

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.

O O

Br
+ + Br

Nucleophile Electrophile Leaving Group


Answer:
Difficulty: Medium
Learning Objective 1: Introduction to Substitution Reactions
Section Reference 1: 7.1
10) What is the IUPAC name for the following compound?

A) 3-Fluorobutane
B) 2-Fluorobutane
C) (S)-2-Fluorobutane
D) (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) Chlorocyclopentane
B) 2-Chloro-1-methylcyclopentane
C) 1-Methyl-2-chlorocyclopentane
D) 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) 2-Bromo-4-pentylhexane
B) (2S,4S)-2-Bromo-4,5-diethylheptane
C) 3,4-Diethyl-6-bromoheptane
D) 2-Bromo-4-methylhexane
E) (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) 1,2-bromocyclopentane
B) (1R, 2S)-1,2-dibromocyclopentane
C) (1S, 2S)-1,2-dibromocyclopentane
D) (1S, 2R)-1,2-dibromocyclopentane
E) (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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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:
I

Learning Objective 1: Alkyl Halides


Section Reference 1: 7.2
Difficulty: Hard

23) Which of the following is a primary alkyl halide?

A) (CH3)2CHCH2Cl
B) (CH3)2CClCH2CH3
C) (CH3)2CHCHClCH3
D) (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) (CH3)2CHCH2Cl
B) (CH3)2CClCH3
C) (CH3)2CHCHClCH3
D) (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) (CH3)2CHCH2Cl
B) (CH3)2CClCH2CH3
C) (CH3)2CHCHClCH3
D) (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) 1-Bromo-2-methylpropane
B) 2-Bromopropane
C) 1-Bromobutane
D) 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) 1-Bromo-2-methylpropane
B) 2-Bromopropane
C) 1-Bromobutane
D) 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) primary halide
B) secondary halide
C) tertiary halide
D) 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) When drawing a curved arrow mechanism, the tail of the arrow starts at______.

A) the bond that is being formed


B) the atom with the positive charge
C) the source of electrons that is being moved
D) 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) When drawing a curved arrow mechanism, the head of the arrow goes to____.

A) the bond that is being formed


B) the bond that is being broken
C) the source of electrons that is being moved
D) 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) Which of the following is not a possible step in a substitution reaction?

A) I
B) II
C) III
D) IV
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.

(CH3)3P
Br P(CH3)3
Answer:
Learning Objective 1: Possible Mechanisms for Substitution Reactions
Section Reference 1: 7.3
Difficulty: Hard

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

Cl O Na + NaCl

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 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) Which of the following is the rate equation for the following SN2 reaction?

A) Rate = k[1-bromopropane]
B) Rate = k[NaCN]
C) Rate = k[1-bromopropane] [NaCN]
D) Rate = k[1-bromopropane]2
E) 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 1-
chloro-3-methylbutane is doubled?

A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) 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) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) 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) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) 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) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) 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) I
B) II
C) III
D) IV
E) Both I & II

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

46) Predict the product for the following SN2 reaction.

A) I
B) II
C) III
D) IV
E) Both I & II

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

47) Predict the product for the following SN2 reaction.

A) I
B) II
C) III
D) IV
E) V

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

48) Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) 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) I
B) II
C) III
D) IV
E) 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.

S
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) Which of the following alkyl halides will undergo the fastest SN2 reaction?

A) I
B) II
C) III
D) IV
E) V

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

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

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

54) Rank the following compounds from most to least reactive in an SN2 reaction.

A) I>IV>II>III
B) II>I>IV>III
C) III>IV>I>II
D) IV>I>II>III
E) IV>III>I>II

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

55) Rank the following compounds from most to least reactive in an SN2 reaction.

A) I>IV>II>III
B) II>I>IV>III
C) III>IV>I>II
D) I>III>II>IV
E) IV>III>I>II

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

56) Which of the following alkyl halides will undergo the slowest SN2 reaction?

A) I
B) II
C) III
D) IV
E) 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) I
B) II
C) III
D) IV
E) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) 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 I

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

62) Which of the following is the rate equation for the following SN1 reaction?

A) Rate = k[H2O]
B) Rate = k[1-chloro-1-methylcyclohexane] [H2O]
C) Rate = k[chloride ion]
D) 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) Rate = k[NaI]
B) Rate = k[2-chloro-2-methylpentane] [NaI]
C) Rate = k[chloride ion]
D) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) IV

Answer: B
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Medium
66) Which of the following alkyl halides will undergo the fastest SN1 reaction?

A) I
B) II
C) III
D) IV
E) V

Answer: E
Learning Objective 1: The SN1 Mechanism
Section Reference 1: 7.5
Difficulty: Easy

67) Which of the following alkyl halides will undergo the slowest SN1 reaction?

A) I
B) II
C) III
D) IV
E) 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) I>IV>II>III
B) II>I>IV>III
C) III>IV>I>II
D) IV>I>II>III
E) IV>III>I>II

Answer: D
Learning Objective 1: The SN 1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

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

A) I>IV>II>III
B) II>III>I>IV
C) III>II>I>IV
D) I>III>II>IV
E) 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) I
B) II
C) III
D) IV
E) 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) Which of the following is true about the stereochemistry of SN1 reaction?

A) retention of configuration at the electrophilic center


B) inversion of configuration at the electrophilic center
C) 50:50 mixture of retention and inversion of configuration at the electrophilic center
D) slightly more inversion than retention at the electrophilic center
E) 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) Predict the product for the following SN1 reaction.

A) I
B) II
C) III
D) IV

Answer: A
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

74) Predict the product for the following SN1 reaction.

A) I
B) II
C) III
D) IV

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

75) Predict the product for the following SN1 reaction.

A) I
B) II
C) III
D) IV

Answer: A
Learning Objective 1: The SN1Mechanism
Section Reference 1: 7.5
Difficulty: Easy

76) Predict the product(s) for the following reaction.


HS SH

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) Predict the product(s) for the following reaction.

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

79) Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) 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 H Br Br
OH2
+ 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) Predict the major product for the following reaction.

A) I
B) II
C) III
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) Predict the major product for the following reaction.

A) I
B) II
C) Both II & III
D) Both I & IV
E) 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) I
B) II
C) Both I & III
D) Both II & IV
E) 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) Which of the following compounds will undergo rearrangement in an SN1 reaction?

A) I
B) II
C) III
D) IV
E) V
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) 3-iodo-5-methylheptane
B) 3-iodo-2-methylheptane
C) 3-iodo-3-methylheptane
D) 3-iodoheptane
E) 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) Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Answer: A
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
Difficulty: Easy
91) Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Answer: A
Learning Objective 1: Drawing the Complete Mechanism for an SN2 Reaction
Section Reference 1: 7.7
Difficulty: Easy

92) Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) 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 + H O
H Br 2
Br

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
H Cl OH2
+ 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 OH
H

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-3-
methylbutane?

A) weak nucleophile in a protic solvent


B) weak nucleophile in an aprotic solvent
C) strong nucleophile in a protic solvent
D) 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-3-
methylbutane?

A) weak nucleophile in a protic solvent


B) weak nucleophile in an aprotic solvent
C) strong nucleophile in a protic solvent
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) SN1
B) SN2
C) Either SN1 or SN2
D) 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) OH-
B) NH3
C) CH3OH
D) NH4+
E) All of these

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

105) Which of the following is a strong nucleophile?

A) OH-
B) H2O
C) CH3OH
D) NH4+
E) 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) OH-
B) H2O
C) CH3O-
D) NH3
E) 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) F-
B) Cl-
C) Br-
D) I-
E) All 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) F-
B) Cl-
C) Br-
D) I-
E) All 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) F-
B) Cl-
C) OH-
D) SH-
E) All 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) I
B) II
C) III
D) IV
E) 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) I-
B) II-
C) III
D) IV
E) 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) I-
B) II-
C) III
D) IV
E) 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) protic solvents stabilize anions only


B) aprotic solvents stabilize anions only
C) protic solvents stabilize cations only
D) aprotic solvents stabilize both cations and anions
E) 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) I
B) II
C) III
D) IV
E) 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) I
B) II
C) III
D) 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) I
B) II
C) III
D) IV
E) 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 + OCH(CH3)2
CH3 CH3

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

118) Provide the reagents necessary to carry out the following conversion.

A) H2S in water
B) H2S in DMSO
C) NaSH in water
D) NaSH in DMSO

Answer: D
Learning Objective 1: Selecting Reagents to Accomplish Functional Group
Transformation
Section Reference 1: 7.9
Difficulty: Easy
119) Provide the reagents necessary to carry out the following conversion.

A) HN3 in water
B) HN3 in acetonitrile
C) NaN3 in water
D) NaN3 in acetonitrile

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

120) Provide the reagents necessary to carry out the following conversion.

A) NaCl in water
B) NaCl in ether
C) HCl in water
D) 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) Provide the reagents necessary to carry out the following conversion.

A) NaOH in water
B) NaOH in ether
C) H2O
D) 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.

Answer: 1) TsCl/pyridine2) O Na
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