1. Which of the following alcohols CANNOT be 5.

How many products would result from the

oxidized to a carboxylic acid with KMnO4? following reaction?
O O CH3MgBr H3O+

A.
O
O A. 1
OH B. 2
B.
C. 3
D. 4
OH
C. 6. Benzoyl chloride, PhC(O)Cl, reacts with water to
form benzoic acid, PhCO2H. In this addition-
OH elimination reaction:
D.
A. water acts as a nucleophile, benzoyl chloride
acts as an electrophile, and chloride acts as
2. Which one of these compounds contains a
a leaving group. 

hemiacetal?
B. water acts as a electrophile. benzoyl chloride
acts as a nucleophile, and chloride acts as a
HO OH
leaving group. 

A. H C. both water and benzoyl chloride act as
electrophiles.
HO O D. there are no nucleophiles or electrophiles in
this type of reaction.
B.
7. Reduction of benzoic acid with LiAIH4 gave
HO O
Compound X. Reaction of X with benzoic acid
C. H and a catalytic amount of sulfuric acid would
yield which one of the following compounds?
O O O
D. H O

3. In an ab-unsaturated aldehyde, a nucleophile A.

readily adds to the b-carbon because the p
electrons are delocalized to which atom? O

O
A. The gamma carbon 

B. The beta carbon 
 B.
C. The carbonyl carbon 

O O
D. The carbonyl oxygen 

O
4. Unlike aldehydes and ketones, which undergo
C.
simple nucleophilic addition reactions, acid
halides tend to undergo addition-elimination
O
reactions. This is best explained by:
D.
A. their higher polarity. 

B. their less sterically-congested environment.
C. their higher electrophilicity. 

D. the good leaving-group ability of the halide
ion. 

8. Hydrolysis of which of the following esters would
yield 2-methylbutanoic acid?

A. O

B. O

10. What is the major product of this reaction

O
O
C. O NH2 Heat
H
O

D. O
A.

OH

9. Which one of the following carbonyl compounds HN

would be expected to have the most acidic
proton? B.
O OH
O
HN
A.

O C.

B. O

O N

C. H
D.
O O

D. O O
N