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
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
Rearrangement 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
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