Question

explain in words

The following reaction will not proceed as written. Clearly explain why this reaction will not occur 1. LDA 2. Br

Answer 1

Generally alkylation of enolate is proceeded by SN2 mechanism. Here tertiarty alkyl halide is used.Tertiary alkyl halides never gives SN2 reactions.

In SN2 reaction the leaving of leaving group and attack of nucleophile are simultanous. But the alkyl halide is bulky. Due to the sterric hinderence the reaction is not feasible. The attack of nucleophile is less possible due to the crowded carbon atom.