Chapter 7
1. Which of the following is a substitution reaction?
Br
Br
OOH
Cl Br
A. B.
C. D.
2. Which of the following is a substitution reaction?
A. B.
C. D.
OH OBr
Br SH
3. Which of the following is a substitution reaction?
A. B.
C. D.
OO
O
Cl O
5. Draw an example of a substitution reaction.
6. What is the nucleophile in the following reaction?
Br CN CN Br
A. B. C. D.
+ +
7. What is the electrophile in the following reaction?
Br CN CN Br
A. B. C. D.
+ +
8. What is the leaving group in the following reaction?
Br CN CN Br
A. B. C. D.
+ +
A. carbon
B. bromide
C. hydrogen
D. nitrogen
9. What are two features typical of a leaving group?
10. For the following reaction, label the nucleophile, electrophile, and leaving group.
Br
O
Br
O
++
Br
O
Br
O
++
LG
11. What is the nucleophile in the following reaction?
12. What is the electrophile in the following reaction?
13. What is the leaving group in the following reaction?
A. Sulfur
B. Carbon
C. Hydrogen
D. Iodide
14. Which of the following is the correct IUPAC name of the following structure?
Cl
A. Chlorocyclopentane
B. 2-Chloro-1-methylcyclopentane
C. 1-Methyl-2-chlorocyclopentane
D. 1-Chloro-2-methylcyclopentane
15. Which of the following is the correct IUPAC name of the following structure?
F
A. 3-Fluorobutane
B. 2-Fluorobutane
C. (S)-2-Fluorobutane
D. (R)-2-Fluorobutane
16. Which of the following is the correct IUPAC name of the following structure?
Br
A. 2-Bromo-3-butylpentane
B. (2S)-Bromo-4,5-dimethylheptane
C. 3,4-Dimethyl-6-bromoheptane
D. 2-Bromo-4-methylhexane
17. Which of the following is the correct structure for a compound with the IUPAC
name of 2-bromo-3-methylbutane?
Br Br
Br
Br
A. B. C. D.
18. Which of the following is the correct structure for a compound with the IUPAC
name of 1-iodo-3-ethylcyclohexane?
A. B. C. D.
III I
19. Which of the following is the correct structure for a compound with the IUPAC
name of (2R)-2-fluorobutane?
FF
F
F
A. B. C. D.
20. Which of the following compounds has a tertiary carbon?
A. B. C. D.
21. Provide an IUPAC name for the following compound.
Br Br
22. Provide an IUPAC name for the following compound.
F
Cl
23. On the following compound, label all of the primary, secondary, and tertiary
carbons.
O
O
O
O
1
2
2
2
22
2
23
3
3
24. Identify the labeled carbon as primary, secondary, or tertiary.
O
25. Identify the labeled carbon as primary, secondary, or tertiary.
26. Identify the labeled carbon as primary, secondary, or tertiary.
O
27. Provide a definition of a concerted reaction.
28. Which of the following is a reasonable definition of a concerted reaction?
A. It is a reaction which takes place in a series of steps.
B. It is a reaction which produces a loud noise.
C. It is a reaction in which all bond-breaking and bond-forming occurs at the same
time.
D. It is a substitution reaction.
29. Provide examples of the 4 patterns for steps in the mechanisms of substitution
reactions.
30. Which of the following is not a possible step in a substitution reaction?
Br
CN CN
Br
Br
Br
OH OH2
H
Br
Br
Br Br
A. B.
C.
D.
31. Provide an arrow pushing mechanism for the following reaction.
Cl OMe
Cl
OMe
32. Provide an arrow pushing mechanism and product for the following reaction.
Br
Me3N
33. When drawing an arrow-pushing mechanism, the tail of the arrow starts where?
A. At the bond that is being formed.
B. At the bond that is being broken.
C. At the source of electrons that is being moved.
D. At the location to which the electrons are being moved.
34. When drawing an arrow-pushing mechanism, the head of the arrow goes where?
A. At the bond that is being formed.
B. At the bond that is being broken.
C. At the source of electrons that is being moved.
D. At the location to which the electrons are being moved.
35. Which of the following shows the correct arrow for loss of a bromide leaving
group?
Br Br Br Br
A. B. C. D.
36. Provide an arrow-pushing mechanism for the following (intramolecular) reaction.
Br O
O
Br O
O
37. Which of the following is the rate law for the following SN2 reaction?
Br NaCN CN
A. Rate = k[1-bromopropane]
B. Rate = k[NaCN]
C. Rate = k[NaCN][1-bromopropane]
D. Rate = k[NaCN]2
38. Write the rate law for the following SN2 reaction.
Br NaCN CN
39. Which of the following is the product of the following SN2 reaction?
Cl
NaCN
NC NC NC
A. B. C. D.
40. Which of the following is the product of the following SN2 reaction?
O
Br
OOOO
A. B. C. D.
41. Provide the SN2 product of the following reaction.
O
Cl
42. Provide a mechanism for this reaction.
O
Cl
43. Which of the following is a mechanism for an SN2 reaction?
Br Br
Br
Br
NH3
NH3
Br
A. B.
C. D.
44. Which of the following is the product of the following reaction?
O
I
OOOI
A. B. C. D.
45. Which of the following is the product of the following reaction?
Me3P
O
OMe
Br
A. B. C. D.
O
OMe
Me3PBr
O
OMe
Me2P
O
OMe
Me3P
O
PMe3
Br
46. Which of the following is the product of the following reaction?
NaN3
Br
A. B. C. D.
N3H2NN3H2N
47. What is the product of the following reaction?
S
I
Difficulty Level: Medium
48. What is the product of the following reaction?
Me3P
O
Br
49. From the given starting material, how could you stereospecifically form the given
product?
Br OMe
50. Rank the following substrates from most to least reactive in an SN2 reaction.
MeI I
I
I
A. B. C. D.
A. A>B>C>D
B. D>C>B>A
C. A>C>B>D
D. D>C>B>A
51. Rank the following substrates from most to least reactive in an SN2 reaction.
I
A. B. C. D.
F
BrCl
A. A>B>C>D
B. D>C>B>A
C. C>B>A>D
D. D>C>B>A
52. Rank the following substrates from most to least reactive in an SN2 reaction.
Br
A. B. C. D.
I
Br
Br
A. A>B>C>D
B. D>C>B>A
C. C>B>A>D
D. D>C>A>B
53. Rank the following substrates from most to least reactive in an SN2 reaction.
I
A. B. C. D.
Br
ClCl
A. A>B>C>D
B. C>D>B>A
C. C>B>A>D
D. D>C>B>A
54. Draw a reaction diagram for the following reaction.
Br
NaSH
SH
55. Which of the following is the reaction diagram for an exothermic, concerted
reaction?
56. Given the following rate law, what will happen to the rate if the concentration of
MeI is doubled?
Rate = k[Me3N][MeI]
A. It will be doubled.
B. It will not change.
C. It will decrease in half.
D. It will increase very slightly.
57. Given the following rate law, what will happen to the rate if the concentration of
both reactants is doubled?
Rate = k[Me3N][MeI]
A. It will be doubled.
B. It will not change.
C. It will decrease in half.
D. It will increase 4-fold.
58. Given the following rate law, what will happen to the rate if the concentration of
MeI is doubled and the concentration of Me3N is halved?
Rate = k[Me3N][MeI]
A. It will be doubled.
B. It will not change.
C. It will decrease in half.
D. It will increase very slightly.
59. Which of the following is the rate law for the following reaction?
Cl H2O
A. Rate = k[H2O]
B. Rate = k[H2O][1-chloro-1-methylcyclohexane]
C. Rate = k[1-chloro-1-methylcyclohexane]
D. Rate = k[chloride ion]
60. Provide the rate law for the following reaction.
Cl H2O
61. Draw a reaction diagram for the following SN1 reaction.
Cl H2O
62. Which of the following is a reaction diagram for an SN1 reaction that is
endothermic?
63. Rank the following substrates from most to least reactive in an SN1 reaction.
I
I
I
A. B. C. D.
I
A. A>B>C>D
B. A>B>D>C
C. D>A>B>C
D. D>C>B>A
64. Rank the following substrates from most to least reactive in an SN1 reaction.
Br
I
A. B. C. D.
MeI
Cl
A. A>B>C>D
B. A>B>D>C
C. C>A>B>D
D. C>D>B>A
65. Rank the following substrates from most to least reactive in an SN1 reaction.
Br
Br
A. B. C. D.
Br
Br
A. A>B>C>D
B. A>B>D>C
C. D>A>B>C
D. D>C>B>A
66. Rank the following substrates from most to least reactive in an SN1 reaction.
I
A. B. C. D.
F
BrCl
A. A>B>C>D
B. A>B>D>C
C. C>B>A>D
D. D>A>B>C
67. Why is a tertiary alkyl halide more reactive in an SN1 reaction than a secondary
alkyl halide?
68. Provide a mechanism for the following SN1 reaction.
OH Br
HBr
OH Br
H Br
69. Which of the following is the product of the following reaction?
Br
O
O
A. B. C. D.
OH OO O
O
O
70. Which of the following is the product of the following reaction?
Cl
MeOH
A. B. C. D.
OMe OH
Cl
71. Which of the following is the product of the following reaction?
Br
NaCl
A. B. C. D.
Na Cl Cl
Br
72. Which of the following is the product of the following reaction?
Cl H2O
A. B. C. D.
OH OH
OH
Cl Cl
73. Provide the product of the following reaction.
Br
O
O
74. What is the product of the following reaction. Include stereochemistry.