Addition of Grignard reagents to ketones to give tertiary alcohols

by James

Description: When a ketone is treated with a Grignard reagent, a new C–C bond is formed at the carbonyl carbon. Subsequent addition of acid will then give the alcohol.
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{ 2 comments… read them below or add one }

Rachel Erickson

Confused about Example 4. Grignard is not on the final product, why is this?

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James

That’s because #4 is a trick question! Acid base reactions are fast, relative to Grignard addition – the Grignard reacts with the carboxylic acid in an acid-base reaction, and the carboxylic acid is later protonated with acid workup. Very common trick question!

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