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Geminal halide hydrolysis is an
organic reaction Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organ ...
. The reactants are geminal dihalides with a water molecule or a hydroxide ion. The reaction yields
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
s from
secondary Secondary may refer to: Science and nature * Secondary emission, of particles ** Secondary electrons, electrons generated as ionization products * The secondary winding, or the electrical or electronic circuit connected to the secondary winding i ...
halides or aldehydes from
primary Primary or primaries may refer to: Arts, entertainment, and media Music Groups and labels * Primary (band), from Australia * Primary (musician), hip hop musician and record producer from South Korea * Primary Music, Israeli record label Works * ...
halides.


Reaction mechanism

The first part of the
reaction mechanism In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of ...
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 Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It i ...
) in a similar way. Further hydrolysis yields
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s.


See also

*
Stephen aldehyde synthesis Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen ( OBE/MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl2), hydrochloric acid (HCl) and que ...


References

Substitution reactions {{organic-chemistry-stub