Question

Discuss the mechanism of Reformatsky reaction.

Answer 1

In the first step, the α -bromo ester reacts with zinc to form zinc enolate which is also called as reformatsky enolate.

This formed enolate is less reactive and hence it reacts as the nucleophilic partner in an addition to give α -hydroxy esters.

Hydrolysis takes place and α -hydroxy ester is generated.

Reformatsky Reaction Mechanism

The product α -hydroxy esters are valuable precursors in natural products synthesis and pharmaceuticals. The use of zinc allows the enolate generation without using any Bronsted base which could condense the ketone or aldehyde on itself.

Examples

Predict the products of the following reaction

Reformatsky Reaction Examples