O
52. Identify the electrophilic atom in the following molecule.
O
A. C
B. H
C. O of carbonyl
D. C of carbonyl
53. Identify the electrophilic site in the following molecule.
Br
54. Identify the electrophilic site in the following molecule.
55. Identify the electrophilic site in the following molecule.
O O
B
A. C
B. O
C. B
D. No electrophilic site
56. Identify the electrophilic site in the following molecule.
N
57. Which of the following cannot be a nucleophile?
A. B. C. D.
OH Br
58. Which of the following cannot be a electrophile?
59. Which of the following is hydride?
A. H+
B. H
C. H–
D. H2
60. Draw the structure for hydride.
61. Which of the following is the most stable cation?
A. B. C. D.
62. For the following reaction step, indicate which pattern it belongs to.
OHOH
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
63. For the following reaction step, indicate which pattern it belongs to.
OHMeOH O
H
OMe
H
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
64. For the following reaction step, indicate which pattern it belongs to.
OHMeOH O
H
OMe
H
65. For the following reaction step, indicate which pattern it belongs to.
OH2
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
66. For the following reaction step, indicate which pattern it belongs to.
OH2
OH
H
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
67. For the following reaction step, indicate which pattern it belongs to.
H
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
68. For the following reaction step, indicate which pattern it belongs to.
Br
Br
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
69. What is wrong with the following mechanism?
H2OBr Br
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.
70. What is wrong with the following mechanism?
H2OBr Br
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.
71. Which of the following is the correct mechanism for a nucleophilic attack pattern?
H2OBr Br
H2OBr Br
H2OBr Br
H2OBr Br
A. B.
C. D.
72. Which of the following is the correct mechanism for a loss of leaving group pattern?
OH2
OH2
OH
Br
HBr
H
A. B.
C. D.
73. Identify the sequence of steps in the following reaction.
OHO
H
H
O
H
A. Proton transfer, Proton transfer
B. Proton transfer, Loss of leaving group
C. Nucleophilic attack, Proton transfer
D. Proton transfer, Nucleophilic attack
74. Identify the sequence of steps in the following reaction.
OHOHMeOH O
H
OMe
HO
H
OMe
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
75. Identify the sequence of steps in the following reaction.
NOH
O
OH
NOH2
O
O
N
O
O
O2N
H
O2N
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
76. Identify the sequence of steps in the following reaction.
H Cl Cl Cl
A. Proton transfer, Proton transfer
B. Proton transfer, Loss of leaving group
C. Nucleophilic attack, Proton transfer
D. Proton transfer, Nucleophilic attack
77. What pattern is the second step of this reaction?
NOH
O
OH
NOH2
O
O
N
O
O
O2N
H
O2N
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
78. What pattern is the fourth step of this reaction?
NOH
O
OH
NOH2
O
O
N
O
O
O2N
H
O2N
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
79. What pattern is the second step of this reaction?
H Cl Cl Cl
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
80. What pattern is the second step of this reaction?
NOH
O
OH
NOH2
O
O
N
O
O
O2N
H
O2N
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
81. What pattern is the second step of this reaction?
OHHO HOH2
HO HO
HO
O
H
O
A. Proton Transfer
B. Loss of Leaving Group
C. Nucleophilic Attack
D. Rearrangement
82. What pattern is the second step of this reaction?
OHOHMeOH O
H
OMe
HO
H
OMe
83. Draw arrows for each step of the following reaction.
OHHO HOH2
HO HO
HO
O
H
O
84. Draw arrows for each step of the following reaction.
OH
H
OH2
H
85. Draw arrows for the following reaction.
O
Li Me O
86. Identify the nucleophilic and electrophilic sites in the following reaction.
O
Li Me O
87. Which of the following is the nucleophilic site in the following reaction?
O
Li Me O
A. C of the carbonyl
B. O
C. Li
D. Me of Li-Me
88. Which of the following is the electrophilic site in the following reaction?
O
Li Me O
A. C of the carbonyl
B. O
C. Li
D. Me
89. Identify the nucleophilic and electrophilic sites in the following reaction.
O
Cl HOMe
O
OMe
90. Which of the following is the electrophilic site in the following reaction?
O
Cl HOMe
O
OMe
A. C of carbonyl
B. O of carbonyl
C. Cl
D. O of alcohol
91. Which of the following cations is likely to undergo rearrangement?
A. B. C. D.
92. Will the following cation undergo rearrangement?
93. Will the following cation undergo rearrangement?
94. Will the following cation undergo rearrangement?
95. Will the following cation undergo rearrangement?
96. Which of the following is the structure of the following cation after rearrangement?
A. B. C. D.
97. Which of the following is the structure of the following cation after rearrangement?
A. B. C. D.
98. Which of the following is the structure of the following cation after rearrangement?
A. B. C. D.
99. Draw the structure of the following cation after rearrangement.
100. Draw the structure of the following cation after rearrangement.
101. Draw the mechanism and product for the following cation rearrangement.
102. Draw the mechanism and product for the following cation rearrangement.