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Br
H2O
75. What is the product of the following reaction. Include stereochemistry.
Br H2O
A. B. C. D.
OH OH
OH
Br OH
76. Why does a racemate form at the leaving group carbon in an SN1 reaction?
77. Which of the following is a good leaving group?
A. -OH
B. -CH3
C. -Br
D. -NH2
78. What is the best leaving group in the following compound?
OH
Br
Cl
79. Circle the best leaving group in the following compound.
F
SMe
OH
Cl
80. Which of the following must be protonated in order to be a good leaving group?
A. Cl
B. Br
C. NMe2
D. OH2
81. Which of the following nucleophiles will require a proton transfer step at the end
of the reaction?
A. NMe3
B. I-
C. OH-
D. H2S
82. Provide an example of a nucleophile that will require a proton transfer step at the
end of the reaction.
83. Which of the following alkyl halides would likely undergo rearrangement during
an SN1 reaction?
Br Br
Br
Br
A. B. C. D.
84. Which of the following is the major product for the following SN1 reaction?
H2O
Br
A. B. C. D.
OH
OH
OH2
HO
85. Draw the anticipated major product for the following reaction.
Br H2O
86. Draw an energy diagram for the following reaction.
87. Draw a mechanism for the following reaction.
OH HBr
OH Br
H Br
88. What is the anticipated major product for the following reaction?
HO
HBr
89. What is the mechanism for the following reaction?
Br
HO
H Br
Br
HO
H Br
90. What is the rate law for the following SN1 reaction?
HO
HBr
91. For the following reaction, which of the following is the mechanism?
OH
HBr
A. SN1
B. SN2
C. Protonation
D. Elimination
92. For the following reaction, which of the following is the product?
OH
HBr
A. B. C. D.
OH2OH Br Br
93. For the following reaction, which of the following is the rate law?
OH
HBr
A. k[HBr]
B. k[1-pentanol]
C. k[HBr][1-pentanol]
D. k[HBr]2
94. Draw an energy diagram for the following reaction.
OH
HBr
95. For the following reaction, which of the following is the mechanism?
OH MeI
A. SN1
B. SN2
C. Protonation
D. Elimination
96. For the following reaction, which of the following is the product?
OH MeI
A. B. C. D.
IOOH2
97. For the following reaction, which of the following is the rate law?
OH MeI
E. Rate = k[MeI]
F. Rate = k[t-butanol]
G. Rate = k[MeI][t-butanol]
H. Rate = k[OH]
98. Draw an energy diagram for the following reaction.
OH MeI
99. For the following reaction, provide the mechanism.
I OH
100. For the following reaction, draw the product.
I OH
101. For the following reaction, provide the rate law.
I OH
102. For the following reaction, provide an energy diagram.
I OH
103. What set of reaction conditions should 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
104. What set of reaction conditions should 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
105. What reaction mechanism is most likely for substitution on the following
compound?
Br
A. SN1
B. SN2
C. Either
D. Neither
106. What reaction mechanism is most likely for substitution on the following
compound?
Br
A. SN1
B. SN2
C. Either
D. Neither
107. What reaction mechanism is most likely for substitution on the following
compound?
Cl
A. SN1
B. SN2
C. Either
D. Neither
108. What reaction mechanism is most likely for substitution on the following
compound?
Cl
A. SN1
B. SN2
C. Either
D. Neither
109. What reaction mechanism is most likely for substitution on the following
compound?
I
A. SN1
B. SN2
C. Either
D. Neither
110. What reaction mechanism is most likely for substitution on the following
compound?
Cl
A. SN1
B. SN2
C. Either
D. Neither
111. Is the following nucleophile strong or weak?
I-
A. Strong
B. Weak
C. Not a nucleophile
112. Is the following nucleophile strong or weak?
H2O
A. Strong
B. Weak
C. Not a nucleophile
113. Is the following nucleophile strong or weak?
Li+
A. Strong
B. Weak
C. Not a nucleophile
114. Is the following nucleophile strong or weak?
HO-
A. Strong
B. Weak
C. Not a nucleophile
115. Is the following nucleophile strong or weak?
H2S
A. Strong
B. Weak
C. Not a nucleophile
116. Provide an example of a strong nucleophile.
117. Is the following nucleophile strong or weak?
CN-
A. Strong
B. Weak
C. Not a nucleophile
118. Is the following nucleophile strong or weak?
Na+
A. Strong
B. Weak
C. Not a nucleophile
119. Why do polar aprotic solvents favor SN2 reactions?
120. What type of solvent would be best for obtaining an optically active product in
the following reaction?
Br CN
NaCN
A. polar protic
B. polar aprotic
C. apolar aprotic
D. water
121. Which of the following leaving groups would you expect to be the best?
NMe3NMe2O
O
O
S
O O
F3C
A. B. C. D.
122. Which of the following solvents is not protic?
A. EtOH
B. H2O
C. NH3
D. hexane
123. What type of solvent is ethanol (EtOH)?
A. polar aprotic
B. apolar aprotic
C. polar protic
124. Which reagents would you use for the following reaction?
Br HS
A. H2S in water
B. H2S in DMSO
C. NaSH in water
D. NaSH in DMSO
125. Which reagents would you use for the following reaction?
Cl N3
A. HN3 in water
B. HN3 in acetonitrile
C. NaN3 in water
D. NaN3 in acetonitrile
126. Which reagents would you use for the following reaction?
OH Cl
A. HCl in water
B. HCl in ether
C. NaCl in water
D. NaCl in DMF
127. Which reagents would you use for the following reaction?
O
N
O
N
Br
A. HBr in water
B. NaBr in water
C. Ethyl bromide
D. Ethyl iodide
128. Which reagents would you use for the following reaction?
Cl OH
A. NaOH in water
B. NaOH in acetonitrile
C. Water
D. HCl in water
129. Which reagents would you use for the following reaction?
Br O
A. methanol
B. methanol in acetonitrile
C. NaOMe in water
D. NaOMe in acetonitrile
130. How would you accomplish the following transformation?
Br O
131. How would you accomplish the following transformation?
Cl SH
132. How would you accomplish the following transformation?
N N
Br
133. How would you accomplish the following transformation?
OH N3
134. How would you accomplish the following transformation?
OH Br
135. How would you accomplish the following transformation?
OH Br
136. Which of the following sets of reagents would best accomplish the following
transformation?
OH O S
O2
A.
B.
C.
D.
SO2Cl
pyridine
SO2OH
pyridine
SO2
SO2O
pyridine
137. Which of the following sets of reagents would best accomplish the following
transformation?
A. HBr B. NaBr
C. D.
SO2Cl
pyridine
SO2Cl
pyridine
then NaBr
OH Br
Difficulty Level: Easy
138. Which of the following sets of reagents would best accomplish the following
transformation?
OH Br
A. HBr B. NaBr
C. D.
SO2Cl
pyridine
SO2Cl
pyridine
then NaBr
