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Reformatsky Reaction

April 22, 2013

Reformatsky Reaction  is a organic reaction in which the aldehydes or ketones condenses with α-halo esters in the presence of metallic zinc to form β-hydroxy esters. This reaction is named after a Russian chemist Sergey Nikolaevich Reformatsky in 1887. In this kind of reaction inert solvent like diethyl ether or THF(tetra hydro furan) is used as a solvent.

“Reformatsky reactions are defined as those resulting from metal insertions into carbon-halogen bonds activated by carbonyl, carbonyl derived or carbonyl related groups in vicinal positions with practically all kinds of electrophiles.”

Reformatsky reaction

Initially zinc reacts with α-halo ester to form a organic reagent called reformatsky enolate. It is added to the carbonyl group of aldehyde or ketone to furnish β- hydroxy ester.This is just like Grignard reagent.

Mechanism of the reaction

  • In the first step the α-bromo ester reacts with zinc to form zinc enolate which is also called reformatsky enolate.
  • This formed enolate is less reactive and hence it reacts as the nucleophilic partner in an addition to give β-hydroxy esters.
  • Hydrolysis takes place and β-hydroxy ester is generated.

Reformatsky reaction mechanism

The product β-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

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