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41. Predict the major product(s) of the following reaction.
h
Br2
Br Br
III III IV V
Br
Br
Br Br
BrBr
Br Br Br
A) I
B) I and II
C) I, II, and III
D) I, II, and IV
E) I, II, III, and IV
F) V
42. Compound A has molecular formula C9H20. Compound A produces three
constitutional isomers upon chlorination, and one constitutional isomer upon
bromination. Which of the following are possible structures of Compound A?
III III
IV VVI
43. Predict possible product(s) of the following reaction.
h
Cl2
Cl Cl
Cl
III III IV V
ClCl
A) I
B) I, II
C) I, II, IV, V
D) I, III, IV, V
E) I, II, III, IV, IV
44. Draw the major product(s) of the following reaction. Is the product optically
active? Explain.
h
Br2
45. Draw the major product(s) of the following reaction. Is the product optically
active? Explain.
h
Br2
46. Draw all possible monochlorination products of 3,3-dimethylpentane, including
stereoisomers.
47. Which of the following are possible products of the reaction shown?
h
Br2
Br
Br
Br
Br
Br
III III IV
Br
A) I
B) II
C) III
D) I, III, and IV
E) I and III
48. Which of the following are possible products of the reaction shown?
h
NBS
Br
Br
Br
Br
III III IV
Br
A) I
B) I, II
C) I, II, III
D) I, IV
E) I, III
49. Which of the following are products of the reaction shown?
h
NBS
III III IV
Br Br
Br Br
A) I
B) I, II
C) I, IV
D) I, III
E) I, II, III, IV
50. Compound A has molecular formula C6H12. Upon treatment with NBS and
irradiation with UV light, only two compounds (including stereoisomers) are
formed. Suggest possible structures for compound A.
51. Compound A has molecular formula C6H10. Upon treatment with NBS and
irradiation with UV light, seven compounds (including stereoisomers) are formed.
Suggest possible structures for compound A and draw the products.
52. Upon treatment with NBS and irradiation with UV light, 2-propyl-1-pentene
produces four monobrominated compounds (including stereoisomers). Draw and
name the products of this reaction.
53. Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methyl
produces three monobrominated compounds (including stereoisomers). Draw the
products of this reaction.
54. Upon treatment with NBS and irradiation with UV light, 2-isopropyl-3-methyl-1-
butene reacts to produce two monobrominated compounds. Draw the products of
this reaction.
55. Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts
to produce six monobrominated compounds. Draw the products of this reaction.
Br
Br
Br Br
56. Which of the following compounds would be expected to be least destructive to
the ozone layer?
CCl3F CCl2F2CCl2FCCl2FCCl2FCH3
ABCD
57. Which of the following shows the correct products initially formed (first step)
when ozone absorbs ultraviolet light?
A) O O +O
B) Cl O +O O
C) O O +O
D) + O
O3
58. Use correct arrow formalism to show the second propagation step for the reaction
of a chlorine radical with ozone.
59. Use correct arrow formalism to show the propagation steps for the autooxidation
of diethyl ether.
60. Which of the following is/are expected to be the major product(s) for the reaction
shown below?
+ O2
OOH
OOH
OOH
OOH
III III IV
A) I
B) II
C) III
D) IV
E) I, IV
61. Which of the following is expected to function as an antioxidant?
O
OH
OH
III III IV
A) I
B) II
C) III
D) IV
E) I, II, III, and IV
62. Which term best describes the process shown below?
O
O
O
+
OO
O
OH
+
O
A) neutralization
B) propagation
C) termination
D) initiation
E) elimination
63. Which term best describes the process shown below?
O
O
O
+
OO
O
O
O
A) initiation
B) propagation
C) termination
D) elimination
E) inhibition
64. Predict the major product(s) of the reaction shown below:
HBr
Br
Br Br
Br
I II III IV
A) I
B) II
C) III
D) IV
E) II and III
65. Predict the major product(s) of the reaction shown below:
HBr
Br
Br Br
Br
I II III IV
ROOR
A) I
B) II
C) III
D) IV
E) II and III
66. Which intermediate leads to the major product for the reaction of 2-methyl-2-
butene with hydrogen bromide and hydrogen peroxide?
Br
I II III IV
Br
A) I
B) II
C) III
D) IV
67. Which intermediate leads to the major product for the reaction of 2-methyl-2-
butene with hydrogen bromide?
Br
I II III IV
Br
A) I
B) II
C) III
D) IV
E) None of the above
68. Predict the product(s) of the following reaction:
HBr
ROOR
Br Br Br Br
III III IV
A) I
B) II
C) III
D) IV
E) I, II
F) I, II, III, IV
69. Predict the product(s) of the following reaction:
Br Br Br
III III IV
HBr
Br
A) I
B) II
C) III
D) IV
E) I, II
F) I, II, III, IV
70. Predict the product(s) of the following reaction:
