SolutionsReaction of organocuprates and organocadmium compounds with acyl halides
1. Ketone, not tertiary alcohol
What is obtained when benzoyl chloride is treated with: a) lithium dimethylcuprate; b) two equivalents of methylmagnesium bromide?
- Acetophenone. The cuprate attacks only the highly activated acid chloride and does not react with the ketone formed.
- 2-Phenyl-2-propanol. The Grignard reagent attacks the acid chloride to give acetophenone, which also reacts with it and is converted into the tertiary alcohol.
2. Synthesis of a ketone
Propose a synthesis of 4-methyl-2-pentanone from an acid chloride and an organometallic reagent.
There are two possibilities: acetyl chloride with lithium diisobutylcuprate, [(CH3)2CHCH2]2CuLi, or 3-methylbutanoyl chloride with lithium dimethylcuprate, (CH3)2CuLi. The corresponding organocadmium reagents (R2Cd) also work.