Hunsdiecker reaction

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The Hunsdiecker reaction (or Borodin reaction) is the organic reaction of silver salts of carboxylic acids with halogens, which gives organic halides. It is an interesting example of a halogenation reaction.

Reaction mechanism

The reaction can be written as:

R-COOAg + Br2 → R-Br + CO2 + AgBr

If iodine is used instead of bromine, the final product will be an ester of the carboxylic acid and its corresponding alcohol. This version is called Simonini reaction.

2 R-COOAg + I2 → R-C(=O)O-R + CO2 + 2 AgI

Procedure

To a solution of silver carboxylate in carbon tetrachloride, elemental bromine is added.

Uses

The Hunsdiecker reaction is useful for making organic halides from silver carboxylates, such as methyl bromide from silver acetate.

References

Relevant Sciencemadness threads