Question

Please write the following mechanism with all of the intermediates, using a carboxylic acid derivative transformation:

Benzoyl chloride + LDA ---> N,N-diisopropyl benzamide

Thank you

Answer 1

LDA is primarily a base used to extract the acidic enol H from aldehyde/ ketones.

But benzoyl chloride doesn't have any such enolisable H. Hence, here, LDA behaves as a nucleophile and attacks the C of C=O group.

The carboxylic acid derivative transformation occuring is : acid chloride to amide

ce Benzoyl chloride : This c should contain enolisable proton. But it doesn't LDA, Lit iz; iz: => nucleophile Reaction : Og Le el ê To z: het Z (N,N diisopropyl benzamide.)