Geminal halide hydrolysis

Geminal halide hydrolysis is an organic reaction.

The reactants are geminal dihalides with a water molecule or a hydroxide ion.

[3][4] The first part of the reaction mechanism consists of an ordinary nucleophilic aliphatic substitution to produce a gem-halohydrin: The remaining halide is a good leaving group and this enables the newly created hydroxy group to convert into a carbonyl group by expelling the halide: Other functional groups can undergo similar hydrolysis reactions.

For instance, geminal trihalides (e.g. benzotrichloride) can be partially hydrolyzed to acyl halides (e.g. benzoyl chloride) in a similar way.

[5] Further hydrolysis yields carboxylic acids.