Difference between revisions of "Hunsdiecker reaction"
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The reaction can be written as: | The reaction can be written as: | ||
| − | :R-COOAg + Br<sub>2</sub> → R-Br + CO<sub>2</sub> + AgBr | + | : R-COOAg + Br<sub>2</sub> → R-Br + CO<sub>2</sub> + 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. | 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 + I<sub>2</sub> → R-C(=O)O-R + CO<sub>2</sub> + 2 AgI | + | : 2 R-COOAg + I<sub>2</sub> → R-C(=O)O-R + CO<sub>2</sub> + 2 AgI |
==Procedure== | ==Procedure== | ||
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=9855 Bromobenzene via the Hunsdiecker reaction?] | *[http://www.sciencemadness.org/talk/viewthread.php?tid=9855 Bromobenzene via the Hunsdiecker reaction?] | ||
*[http://www.sciencemadness.org/talk/viewthread.php?tid=66503 Halobenzenes by decarboxylation of halobenzoic acids] | *[http://www.sciencemadness.org/talk/viewthread.php?tid=66503 Halobenzenes by decarboxylation of halobenzoic acids] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=83518 Hunsdiecker Reaction with Amino Acids Literature/Insight] | ||
[[Category:Reactions]] | [[Category:Reactions]] | ||
Latest revision as of 21:56, 15 May 2020
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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.
