Question
In order to perform C-ethylation of acetone, it must first be treated with one equivalent of...
In order to perform C-ethylation of acetone, it must first be treated with one equivalent of an amine, followed by one equivalent of bromoethane, and then subjected to hydrolysis. Which of the following amines will be the best choice for this synthesis?
A) Piperidine
B) Ethylamine
C) Methylamine
D) Trimethylamine
E) 2-Aminohexane
Homework Answers
Answer #1
The provided reaction is an example of the Stork-enamine
alkylation reaction. Stork enamine alkylation reaction involves the
reaction of enol form of the ketone with a cyclic secondary amine
to form enamine ( 
-unsaturated
amine). Enamines are nucleophilic and react with the alkyl halide
and the product upon hydrolysis results in the alkylated ketone.
Enamines derived from cyclic secondary amines are more stable than
enamines derived from acyclic secondary amines. Therefore here, the
suitable amine is Piperidine
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