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

Science   Chemistry   
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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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