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[1] or aldehydes from primary halides.[2][3]

Reaction mechanism

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

RCH(Cl)2 + H2O {\textstyle \longrightarrow} RCH(Cl)OH + HCl

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(Cl)OH {\textstyle \longrightarrow} RCHO + 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.[4] Further hydrolysis yields carboxylic acids.

See also

References

  1. ↑ Marvel, C. S.; Sperry, W. M. (1928). "Benzophenone". Organic Syntheses 8: 26. doi:10.15227/orgsyn.008.0026.
  2. ↑ Bill, J. C.; Tarbell, D. S. (1954). "o-Phthalaldehyde". Organic Syntheses 34: 82. doi:10.15227/orgsyn.034.0082.
  3. ↑ Buck, Johannes S.; Zimmermann, F. J. (1938). "Protocatechualdehyde". Organic Syntheses 18: 75. doi:10.15227/orgsyn.018.0075.
  4. ↑ Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry: 139. doi:10.1002/14356007.a06_233.pub2.
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