This is a free preview. For full access
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...
Show More
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 ...
Show More