Organic Chemistry 2nd Edition Klein

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Chapter 6

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium

1. Estimate the enthalpy change of the following reaction under standard conditions.

Ans: +8 kJ/mol

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium

2. Estimate the enthalpy change of the following reaction under standard conditions.

Ans: +29 kJ/mol

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium

3. Estimate the enthalpy change of the following reaction under standard conditions.

Ans: -8 kJ/mol

Topic: Enthalpy
Section 6.1
Difficulty Level: Easy

4. Which of the following is the enthalpy change of the following reaction under
standard conditions?

A. -8 kJ/mol
B. +8 kJ/mol
C. +222 kJ/mol
D. +79 kJ/mol
Ans: B

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium
 5. Which of the following is the enthalpy change of the following reaction under
standard conditions?

A. -8 kJ/mol
B. +8 kJ/mol
C. -506 kJ/mol
D. +63 kJ/mol
Ans: A

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium

6. Later in the course, we will compare the halogenation of differently substituted

carbons, comparing reactions like the ones below. Which of the following
statements is true about reactions A and B?

A. Both reactions have a positive heat of reaction (Ho)

B. Neither reaction has a positive heat of reaction (Ho)
C. Only reaction A has a positive heat of reaction (Ho)
D. Only reaction B has a positive heat of reaction (Ho)
Ans: B

Topic: Enthalpy
Section 6.1
Difficulty Level: Medium

7. Later in the course, we will compare the halogenation of differently substituted

carbons, comparing reactions like the ones below. Which of the following
reactions has a more exothermic heat of reaction (Ho)?

A. Reaction A has a more exothermic heat of reaction (Ho)

B. Reaction B has a more exothermic heat of reaction (Ho)
C. Both reactions have the same heat of reaction (Ho)
Ans: B
Topic: Enthalpy
Section 6.1
Difficulty Level: Hard

8. You are working in a research laboratory and have developed a new reagent that
cleaves C-H bonds homolytically. Unfortunately, this reagent can achieve only one
of the transformations shown below. In light of bond dissociation energies, which
transformation is most likely to be achieved?

Ans: A

Topic: Enthalpy
Section 6.1
Difficulty Level: Easy

9. What type of bond cleavage does the following reaction involve?

A. homolytic
B. heterolytic
Ans: A

Topic: Enthalpy
Section 6.1
Difficulty Level: Easy

10. What type of bond cleavage does the following reaction involve?

Ans: heterolytic

Topic: Entropy
Section 6.2
Difficulty Level: Easy

11. Predict the sign of S of the following reaction.

A. positive
B. negative
C. no change
Ans: B

Topic: Entropy
Section 6.2
Difficulty Level: Easy

12. Predict the sign of S of the following reaction.

A. positive
B. negative
C. no change
Ans: A

Topic: Entropy
Section 6.2
Difficulty Level: Easy

13. Predict the sign of S of the following reaction.

A. positive
B. negative
C. no change
Ans: B

Topic: Entropy
Section 6.2
Difficulty Level: Medium

14. Predict the sign of S of the following reaction.

Ans: positive

Topic: Entropy
Section 6.2
Difficulty Level: Medium
 15. Predict the sign of S of the following reaction.

Ans: negative

Topic: Entropy
Section 6.2
Difficulty Level: Hard

16. Why is the entropy change negative for ring closures?

A. Closing a ring results in fewer molecules.
B. Closing a ring results in more molecules.
C. Closing a ring releases energy.
D. Closing a ring restricts the rotation around individual carbon-carbon bonds.
Ans: D

Topic: Entropy
Section 6.2
Difficulty Level: Hard

17. Which of the following would you expect to have the most negative S?

Ans: D

Topic: Entropy
Section 6.2
Difficulty Level: Hard

18. Of following reactions, which one(s) would you expect to have a negative S?
Ans: A and B

Topic: Gibbs Free Energy

Section 6.3
Difficulty Level: Easy

19. Predict the sign of G for an exothermic reaction with an increase in entropy.
A. positive
B. negative
C. no change
D. cannot predict without additional information
Ans:B

Topic: Gibbs Free Energy

Section 6.3
Difficulty Level: Easy

20. Predict the sign of G for an endothermic reaction with an increase in entropy.
A. positive
B. negative
C. no change
D. cannot predict without additional information
Ans:D

Topic: Gibbs Free Energy

Section 6.3
Difficulty Level: Easy

21. Predict the sign of G for an exothermic reaction with a decrease in entropy.
A. positive
B. negative
C. no change
D. cannot predict without additional information
Ans:D

Topic: Gibbs Free Energy

Section 6.3
Difficulty Level: Easy

22. Predict the sign of G for an endothermic reaction with a decrease in entropy.
A. positive
B. negative
C. no change
D. cannot predict without additional information
Ans:A

Topic: Equilibria
Section 6.4
Difficulty Level: Easy

23. Does a reaction with a positive G favor reactants or products?

Ans: Reactants

Topic: Equilibria
Section 6.4
Difficulty Level: Easy

24. Does a reaction with a negative G favor reactants or products?

Ans: Products

Topic: Equilibria
Section 6.4
Difficulty Level: Hard

25. Does a reaction with a positive S and a positive H favor reactants or products?
Ans: Cannot determine without additional information

Topic: Equilibria
Section 6.4
Difficulty Level: Hard

26. Does a reaction with a positive S and a negative H favor reactants or products?
Ans: Products

Topic: Equilibria
Section 6.4
Difficulty Level: Easy

27. Does a reaction with a Keq = 10 favor reactants or products?

Ans: Products

Topic: Equilibria
Section 6.4
Difficulty Level: Hard

28. Does a reaction with a H of 14 kJ/mol and a S of 150 J/molK at 298 K favor
reactants or products?
Ans: Products

Topic: Equilibria
Section 6.4
Difficulty Level: Hard

29. Does a reaction with a H of 20 kJ/mol and a S of 10 J/mol K at 298 K favor

reactants or products?
Ans: Reactants

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

30. Given the following rate law, what is the order of the reaction with respect to
MeI?

Ans: first

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

31. Given the following rate law, what is the order of the reaction with respect to
tert-butyl iodide?

Ans: first

Topic: Kinetics
Section 6.5
Difficulty Level: Easy
 32. Given the following rate law, what is the order of the reaction with respect to
sodium cyanide?

Ans: second

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

33. What is the energy of activation for the following reaction?

Ans: 10 kJ/mol

Topic: Kinetics
Section 6.5
Difficulty Level: Hard

34. What is the energy of activation for the following reaction?

Ans: 10 kJ/mol

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

35. Based on the following energy diagram, is the reaction exothermic or

endothermic?
Ans: exothermic

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

36. Based on the following energy diagram, is the reaction exothermic or

endothermic?

Ans: endothermic

Topic: Kinetics
Section 6.5
Difficulty Level: Hard

37. What is the effect of a catalyst on a reaction?

A. It increases the rate.
B. It decreases the entropy.
C. It changes the equilibrium.
D. It makes the products more stable.
Ans: A

Topic: Kinetics
Section 6.5
Difficulty Level: Easy

38. Which of the following describes the effect of a catalyst on a reaction?

A. It lowers the free energy of the products.
B. It makes the reactants less stable.
C. It changes the equilibrium constant.
D. It lowers the energy of activation.
Ans: D

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

39. Which of the following is an energy diagram for a three-step reaction?

Ans: B

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

40. Which of the following is an energy diagram for a two-step reaction?

Ans: B

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

41. Draw an energy diagram for an endothermic reaction with two steps.
Ans:

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

42. Draw an energy diagram for a three-step reaction.

Ans:

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Hard

43. Draw an energy diagram for a concerted exothermic reaction.

Ans:

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

44. Which of the following energy diagrams shows a concerted endothermic reaction?
Ans: D

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Medium

45. Which of the following energy diagrams shows the reaction with the smallest
energy of activation?

Ans: A

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Easy

46. What is a transition state?

A. An isolable intermediate in a reaction.
B. The starting materials of the reaction.
C. A local maximum on the energy diagram.
D. A low-energy point between the starting materials and the product.
Ans: C

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Easy

47. What is an intermediate?

A. A local maximum on the energy diagram.
B. A point on the reaction pathway that has a discrete lifetime.
C. A point half-way between the starting materials and products.
D. The highest energy compound on an energy diagram.
Ans: B
Topic: Reading Energy Diagrams
Section 6.6
Difficulty Level: Easy

48. Which of the following energy diagrams is of a reaction with one transition state?

Ans: A

Topic: Reading Energy Diagrams

Section 6.6
Difficulty Level: Easy

49. Which of the following energy diagrams is of a reaction with one intermediate?

Ans: B

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

50. Identify the nucleophilic site in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

51. Identify the nucleophilic site in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Hard

52. Identify the nucleophilic site(s) in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Medium

53. Identify the nucleophilic centers in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

54. Identify the nucleophilic atom in the following molecule.

A. P
B. C
C. H
D. Me
Ans: A

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Hard

55. Identify the electrophilic site in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

56. Identify the electrophilic site in the following molecule.

A. H
B. C of carbonyl
C. C other than carbonyl
D. O of carbonyl
Ans: B

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Medium

57. Identify the electrophilic site in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

58. Identify the electrophilic site in the following molecule.

Ans:

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Hard

59. Identify the electrophilic site in the following molecule.

A. C
B. O
C. B
D. No electrophilic site
Ans: C

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

60. Which of the following cannot be a nucleophile?

Ans; A

Topic: Nucleophiles and Electrophiles

Section 6.7
Difficulty Level: Easy

61. Which of the following cannot be an electrophile?

Ans: D

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

62. Which of the following is hydride?

A. H+
B. H
C. H−
D. H2
Ans: C

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Medium

63. Draw the structure of hydride.

Ans:

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

64. Which of the following is the most stable cation?

Ans: C

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

65. For the following reaction step, indicate which pattern of arrow pushing it
represents.

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: A

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy
 66. For the following reaction step, indicate which pattern of arrow pushing it
represents.

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: C

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Medium

67. For the following reaction step, indicate which pattern of arrow pushing it
represents.

Ans: Nucleophilic attack

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

68. For the following reaction step, indicate which pattern of arrow pushing it
represents.

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: B

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

69. For the following reaction step, indicate which pattern of arrow pushing it
represents.
A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: A

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

70. For the following reaction step, indicate which pattern of arrow pushing it
represents.

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: D

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

71. For the following reaction step, indicate which pattern of arrow pushing it
represents.

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: C

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Medium
 72. Melphalan, a drug used in chemotherapy, reacts with itself in the body before
binding with its target, as illustrated in the mechanism below. Which two patterns
of arrow pushing are seen in this reaction?

Ans. Nucleophilic attack and loss of leaving group

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Medium

73. Melphalan, a drug used in chemotherapy, reacts with itself before binding with its
target in the body, as illustrated below. Draw in the curved arrows that account
for this transformation.

Ans.

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Medium

74. The following reaction has three mechanistic steps. Draw all curved arrows
necessary to complete the mechanism.
Ans.

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

75. What is wrong with the following mechanism?

A. There is no leaving group, so there should be no arrows.

B. The arrow should be removing a proton from the H2O group.
C. An arrow is also needed to indicate the loss of the leaving group.
D. The arrow is backwards.
Ans: C

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Hard

76. What is wrong with the following mechanism?

A. There is no leaving group, so there should be no arrows.

B. The arrow should be removing a proton from the H2O group.
C. An arrow is also needed to indicate the loss of the leaving group.
D. The arrow indicating the formation of the C-Br bond (nucleophilic attack) should start
at the bromide anion.
Ans: D

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy
 77. Which of the following mechanistic steps represents a nucleophilic attack?

Ans: B

Topic: Mechanisms and Arrow Pushing

Section 6.8
Difficulty Level: Easy

78. Which of the following mechanistic steps represents the loss of a leaving group?

Ans: C

Topic: Combining Patterns

Section 6.9
Difficulty Level: Easy

79. Identify the sequence of curved arrows (electron movement) in the steps of the
following reaction.

A. Proton transfer, proton transfer

B. Proton transfer, loss of leaving group
C. Nucleophilic attack, proton transfer
D. Proton transfer, nucleophilic attack
Ans: A
Topic: Combining Patterns
Section 6.9
Difficulty Level: Medium

80. The following reaction has three mechanistic steps. Identify the pattern of arrow
pushing steps in each step.

Ans. Proton transfer; loss of leaving group, nucleophilic attack

Topic: Combining Patterns

Section 6.9
Difficulty Level: Hard

81. Identify the sequence of curved arrows (electron movement) in the steps of the
following reaction.

A. Proton transfer, proton transfer, nucleophilic Attack

B. Proton transfer, loss of leaving group
C. Nucleophilic attack, proton transfer, loss of leaving group
D. Proton transfer, nucleophilic attack, proton transfer
Ans: D

Topic: Combining Patterns

Section 6.9
Difficulty Level: Hard

82. Identify the sequence of curved arrows (electron movement) in the steps of the
following reaction.
A. Proton transfer, proton transfer, nucleophilic attack
B. Proton transfer, loss of leaving group, nucleophilic attack, proton transfer
C. Nucleophilic attack, proton transfer, loss of leaving group
D. Proton transfer, loss of leaving group, proton transfer, nucleophilic attack
Ans: B

Topic: Combining Patterns

Section 6.9
Difficulty Level: Easy

83. Identify the sequence of curved arrows (electron movement) in the steps of the
following reaction.

A. Proton transfer, proton transfer

B. Proton transfer, loss of leaving group
C. Nucleophilic attack, proton transfer
D. Proton transfer, nucleophilic attack
Ans: D

Topic: Combining Patterns

Section 6.9
Difficulty Level: Hard

84. What pattern of curved arrow pushing is the second step of this reaction?

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: B

Topic: Combining Patterns

Section 6.9
Difficulty Level: Easy

85. What pattern of curved arrow pushing is the fourth step of this reaction?

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: A

Topic: Combining Patterns

Section 6.9
Difficulty Level: Easy

86. What pattern of curved arrow pushing is the second step of this reaction?

A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: C

Topic: Combining Patterns

Section 6.9
Difficulty Level: Easy

87. What pattern of curved arrow pushing is the second step of this reaction?
A. Proton transfer
B. Loss of leaving group
C. Nucleophilic attack
D. Rearrangement
Ans: B

Topic: Combining Patterns

Section 6.9
Difficulty Level: Hard

88. What pattern of curved arrow pushing is the second step of this reaction?

Ans: Nucleophilic attack

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Hard

89. Draw arrows for each step of the following reaction.

Ans:
Topic: Drawing Curved Arrows
Section 6.10
Difficulty Level: Hard

90. Draw curved arrows for each step of the following reaction.

Ans:

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Hard

91. Draw curved arrows for the following mechanistic step.

Ans:

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Medium
 92. Identify the nucleophilic and electrophilic sites in the reactants of the following
reaction.

Ans:

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Easy

93. Which of the following is the nucleophilic site in the reactants of the following
reaction?

A. C of the carbonyl
B. O
C. Li
D. Me of Li-Me
Ans: D

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Easy

94. Which of the following is the electrophilic site in the reactants of the following
reaction?

A. C of the carbonyl
B. O
C. Li
D. Me
Ans: A

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Medium

95. Identify the nucleophilic and electrophilic sites in the substrate and reagent of the
following reaction.

Ans:

Topic: Drawing Curved Arrows

Section 6.10
Difficulty Level: Easy

96. Which of the following is the electrophilic site in the reactants of the following
reaction?

A. C of carbonyl
B. O of carbonyl
C. Cl
D. O of alcohol
Ans: A

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

97. Which of the following cations is most likely to undergo rearrangement?

Ans: B

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

98. Will the following cation undergo rearrangement?

Ans: Yes

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

99. Will the following cation undergo rearrangement?

Ans: No

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

100. Will the following cation undergo rearrangement?

Ans: Yes

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

101. Will the following cation undergo rearrangement?

Ans: Yes

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

102. Which of the following is the most likely structure of the following cation
after rearrangement?

Ans: D
Topic: Carbocation Rearrangements
Section 6.11
Difficulty Level: Easy

103. Which of the following is the most likely structure of the following cation
after rearrangement?

Ans: A

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Easy

104. Which of the following is the most likely structure of the following cation
after rearrangement?

Ans: B

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Medium

105. Draw the structure of the most likely following cation after it has
rearranged.

Ans:

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Medium

106. Draw the most likely structure of the following cation after it has
rearranged.

Ans:
Topic: Carbocation Rearrangements
Section 6.11
Difficulty Level: Hard

107. Draw the mechanism and most likely product for the following cation
rearrangement.

Ans:

Topic: Carbocation Rearrangements

Section 6.11
Difficulty Level: Hard

108. Draw the mechanism and most likely product for the following cation
rearrangement.

Ans:

Topic: Combining Patterns + Spectroscopy

Section 6.9 + Spectroscopy
Difficulty Level: Medium

109. Consider the product of the following mechanism. How many distinct
resonances would appear in the (proton-decoupled) 13C NMR spectrum for the
product?

A. 2
B. 3
C. 4
D. 5
Ans: C
Topic: Integrated
Section 6.2 and 6.9
Difficulty Level: Medium

110. Consider the following reaction. What patterns of arrow pushing are
likely involved in the formation of the product? Would you expect the S for the
reaction to be positive or negative?

Ans: Proton transfer and loss of a leaving group; S is expected to be positive.