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Exam Name___________________________________

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1)

1) Disregarding stereoisomers, how many different enols can the β-diketone
CH3 COCH 2 COCH 2 CH3 form?
A) 3

B) 1

C) 4

D) 0

E) 2

2) Methylamine reacts with acetophenone to yield the:
A) imine.
B) enamine.
C) acetal.
D) amide
E) iminium salt.

2)

3) What product results when an aldol is dehydrated?
A) β-diketone
B) β-ketoester
C) conjugated alkyne
D) β,γ-unsaturated aldehyde
E) α,β-unsaturated aldehyde

3)

4) Which of the following will react most slowly with an enamine?
A) methyl bromide
B) allyl bromide
C) acetyl chloride
D) isopropyl chloride
E) benzyl chloride

4)

5) What type of product results when 3-pentanone reacts with dimethylamine?
A) enolate
B) enol
C) enamine
D) imine

5)
E) amide

6) The relationship between ketones and their corresponding enols is one of:
A) enantiomers
B) diastereomers.
C) tautomers.
D) cis-trans isomers.
E) allotropes.

6)

7) Which of the following ketones will give a positive iodoform test?
A) 2-methyl-3-pentanone
B) 3-hexanone
C) 4-heptanone
D) 2-hexanone
E) cyclohexanone

7)

1

8) Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?
A) lithium diisopropylamide
B) lithium hydroxide
C) methyllithium
D) pyridine
E) diethylamine

8)

9) The α-halogenation of cyclohexanone:
A) is slowed by the presence of acid.
B) is catalyzed by base.
C) requires one equivalent of base.
D) is catalyzed by the sodium halide salt.
E) requires one equivalent of acid.

9)

10) In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a:
A) 1,2-fashion.
B) 1,3-fashion.
C) 1,4-fashion.
D) 1,5-fashion.
E) Diels-Alder reaction.

10)