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HIGH SCHOOL

Chemistry

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Organic Chemistry

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α-Carbon Chemistry: Enols, Enolates, and Enamines

Ketone Enolate Formation Depends on Base

Description

Ketone α-alkylation depends on how the base forms the enolate ion. The reaction uses alkyl halides and a base. The enolate then acts as a nucleophile and undergoes nucleophilic substitution.

The base is the key factor in the reaction outcome. A base such as EtO− has a conjugate acid, EtOH, with p...

Transcript

Recall that α-alkylation of ketones occurs via the generation of an enolate ion followed by a substitution reaction.

The enolate formation from ketones takes place in the presence of a base that plays a crucial role in deciding the reaction outcome.

A base whose conjugate acid is stronger than the ketone favors the reverse ...

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