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14.14: Acid Halides to Alcohols: Grignard Reaction

JoVE Core
Organic Chemistry

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Acid Halides to Alcohols: Grignard Reaction

14.14: Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.

Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs, forming a ketone. The addition of another equivalent of the carbanion generates a tertiary alkoxide ion. Protonation of the alkoxide gives a tertiary alcohol as the final product.



Acid Halides Grignard Reaction Grignard Reagents Tertiary Alcohols Ketone Intermediate Carbanions Nucleophiles Carbonyl Carbon Tetrahedral Intermediate Halide Ion Ketone Tertiary Alkoxide Ion Protonation Final Product

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