CHEM 232 Fall Exam 2 Questions with Verified Solutions
1. Which of these is the best leaving group?
Best leaving group is weakest
base
2 a. e. OH–
3 c. (has strongest conjugate acid).
d. Can also determine by anion
b. CH3O–
stability (correct answer
delocalizes charge to most
2. Which of these choices is the strongest nucleophile in acetone? Acetone is an aprotic solvent, so
nucleophilicity = basicity.
e.
a. Cl– 3 c. SH– OH–
b. CH3CO2– d. F–
3. Which of these ammonium ions has the strongest conjugate base?
d. acid (highest pKa)
Weakest
has
a.
strongest conjugate base.
b. e. The conjugate bases of all these ammonium
ions are equally basic.
3 c.
4. Which is the most likely product of the reaction shown here?
E2 (strong base) with
conformational restriction =
syn elimination (POTD 19
#17)
a. c. These conditions will not
3 e.
lead to any reaction.
b. 2 d.
1
, 5. Which of the following compounds is the major product of this reaction?
Nitration conditions with an
Electron Withdrawing Group
= meta nitration.
3 a. 2 c. e.
b. d.
6. Which of the following compounds is the major product of this reaction?
Strong base and tertiary leaving group = E2 (no
SN2/SN1/
E1). Eliminates from anti conformation.
a. 3 c.
e.
b. d.
7. Which of the following compounds is the major product of this reaction?
Friedel-Crafts Alkylation with electron donating
substitutent on
ring = o/p substitution. Secondary carbocation
susceptible to rearrangement by methyl shift to give
tertiary cation.
a. 3 c. e.
2 b. d.
2
1. Which of these is the best leaving group?
Best leaving group is weakest
base
2 a. e. OH–
3 c. (has strongest conjugate acid).
d. Can also determine by anion
b. CH3O–
stability (correct answer
delocalizes charge to most
2. Which of these choices is the strongest nucleophile in acetone? Acetone is an aprotic solvent, so
nucleophilicity = basicity.
e.
a. Cl– 3 c. SH– OH–
b. CH3CO2– d. F–
3. Which of these ammonium ions has the strongest conjugate base?
d. acid (highest pKa)
Weakest
has
a.
strongest conjugate base.
b. e. The conjugate bases of all these ammonium
ions are equally basic.
3 c.
4. Which is the most likely product of the reaction shown here?
E2 (strong base) with
conformational restriction =
syn elimination (POTD 19
#17)
a. c. These conditions will not
3 e.
lead to any reaction.
b. 2 d.
1
, 5. Which of the following compounds is the major product of this reaction?
Nitration conditions with an
Electron Withdrawing Group
= meta nitration.
3 a. 2 c. e.
b. d.
6. Which of the following compounds is the major product of this reaction?
Strong base and tertiary leaving group = E2 (no
SN2/SN1/
E1). Eliminates from anti conformation.
a. 3 c.
e.
b. d.
7. Which of the following compounds is the major product of this reaction?
Friedel-Crafts Alkylation with electron donating
substitutent on
ring = o/p substitution. Secondary carbocation
susceptible to rearrangement by methyl shift to give
tertiary cation.
a. 3 c. e.
2 b. d.
2
