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Geminal halide hydrolysis

Geminal halide hydrolysis is an organic reaction. The reactants are geminal dihalides with a water molecule or a hydroxide ion. The reaction yields ketones from secondary halides or aldehydes from primary halides.

Reaction mechanism

The first part of the reaction mechanism consists of an ordinary nucleophilic aliphatic substitution to produce a gem-halohydrin:

: RCH(Cl)2 + KOH \longrightarrow RCH(OH)Cl + KCl

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:

:RCH(OH)Cl \longrightarrowRearrangement gives R-CHO + HCl

Variations

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. Further hydrolysis yields carboxylic acids.

References

References

  1. (1928). "Benzophenone". Organic Syntheses.
  2. (1899). "The Action of Sodium Methylate Upon Dibromides of Propenyl-Compounds and of Unsaturated Ketones". Journal of the American Chemical Society.
  3. (1954). "o-Phthalaldehyde". Organic Syntheses.
  4. (1938). "Protocatechualdehyde". Organic Syntheses.
  5. (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry.
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