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Reaction of organocuprates and organocadmium compounds with acyl halides

Organocuprates and organocadmium compounds are organometallic reagents very different from organolithium and Grignard reagents. Their C–metal bonds are much less ionic and the carbon is much less nucleophilic.

Organocadmium and acyl halides▶ Watch the video on YouTube
Reaction of an acyl chloride with an organocuprate or an organocadmium compound: ketone

They are much weaker nucleophiles, able to attack only very activated carbonyl groups such as acyl chlorides. The resulting ketone cannot be attacked by these Cu and Cd organometallic reagents.