Why is the use of dialkyl cadmium () synthetically preferred over traditional Grignard reagents () for the preparation of ketones from acyl chlorides?

Question

Why is the use of dialkyl cadmium ($R_2Cd$) synthetically preferred over traditional Grignard reagents ($RMgX$) for the preparation of ketones from acyl chlorides?

Prashant Kotian · Accepted Answer

Correct answer: C. Grignard reagents are highly reactive nucleophiles. Once the acyl chloride is converted to a ketone, the Grignard reagent will attack the newly formed ketone to produce a 3° alcohol. Dialkyl cadmium is less reactive; it acts as a nucleophile towards the highly electrophilic acyl chloride but is unreactive towards the resulting ketone, halting the reaction at the desired ketone stage.

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