Which reagent converts benzoyl chloride to acetophenone, stopping at the ketone stage in high yield?

A $(CH X_{3}) X_{2} CuLi$ (1 equiv), THF, $-78\,^\circ\mathrm{C}$
B $NaBH X_{4}$ , methanol
C $CH X_{3} Li$ (2 equiv), ether
D $CH X_{3} MgBr$ (3 equiv), ether, room temperature

Answer: A

Grignard and organolithium reagents add to the ketone product, giving tertiary alcohols. The less reactive lithium dialkylcuprate reacts with the very reactive acid chloride but not with the ketone product, so it stops at acetophenone.

NaBH X_{4}

would give a reduction product (benzyl alcohol), not the ketone.

Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Nucleophilic acyl substitution of carboxylic acid derivatives

Previous questionNext question

Which reagent converts benzoyl chloride to acetophenone, stopping at the ketone stage in high yield?

Answer: A

More questions on Nucleophilic acyl substitution of carboxylic acid derivatives