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?
2) Methylamine reacts with acetophenone to yield the:
E) iminium salt.
3) What product results when an aldol is dehydrated?
C) conjugated alkyne
D) β,γ-unsaturated aldehyde
E) α,β-unsaturated aldehyde
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
5) What type of product results when 3-pentanone reacts with dimethylamine? A) enolate
6) The relationship between ketones and their corresponding enols is one of: A) enantiomers
D) cis-trans isomers.
7) Which of the following ketones will give a positive iodoform test? A) 2-methyl-3-pentanone
8) Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt? A) lithium diisopropylamide
B) lithium hydroxide
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.
10) In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a: A) 1,2-fashion.
E) Diels-Alder reaction.
11) (S)-2-Methylbutanal __________ upon sitting in an acidic or a basic aqueous solution. A) inverts completely to the R configuration
C) irreversibly forms the hydrate
12) The Hell-Volhard-Zelinsky reaction involves:
A) the α-bromination of ketones.
B) the bromination of alcohols.
C) the α-bromination of carboxylic acids.
D) the oxidation of aldehydes to acids.
E) none of the above.
13) When a ketone and its enol are in equilibrium, under most conditions the concentration of the enol is __________ the concentration of the ketone.
A) equal to
B) much higher than
C) much lower than
D) slightly higher than
E) exactly half of
14) When 2-methylcyclohexanone is treated with catalytic base in excess D 2 O, how many deuterium
atoms become incorporated in the organic compound?
15) An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this?
A) an acid-catalyzed aldol condensation
B) a base-mediated aldol condensation
C) a Selman-Jones reaction
D) a Hell-Volhard-Zelinsky reaction
E) a Fischer esterification
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 16) Provide the structure of the aldol product that results when 5-methylhexanal is treated with hydroxide.
17) What two organic starting materials are required to produce cinnamaldehyde (PhCHCHCHO) via a crossed aldol condensation followed by dehydration?
18) Complete the following synthesis by filling in the missing reagents.
19) Provide a detailed, stepwise mechanism for the a -bromination of acetone in base.
20) Provide the major organic product of the following reactions.
21) What compound is produced in the reaction of cyclopentanone with Br 2 in acetic acid?
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