How do Grignard reagents react with ketones to form tertiary alcohols?
Grignard reagents (RMgX) are highly reactive organometallic compounds that function as strong nucleophiles, behaving similarly to carbanions.12
When a Grignard reagent reacts with a ketone, the nucleophilic carbon of the reagent attacks the electrophilic carbonyl carbon of the ketone. This addition process forms a new carbon-carbon bond, resulting in an intermediate alkoxide. Subsequent treatment with aqueous acid protonates this intermediate to yield a tertiary alcohol.132
This reaction is a fundamental tool in synthetic organic chemistry for assembling complex carbon skeletons. While the reaction with formaldehyde produces primary alcohols and other aldehydes produce secondary alcohols, the specific use of ketones is the standard method for synthesizing tertiary alcohols.13