Geminal halide hydrolysis: Difference between revisions
No. In the haloform reaction alpha-keto-1,1,1-halides are cleaved to yield haloform + carboxylate. |
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'''Geminal halide hydrolysis''' is an [[organic reaction]]. The reactants are a [[geminal]] [[halide|dihalide]] and [[water]] or a [[hydroxide]]. The reaction product is a [[ketone]] or an [[aldehyde]]. 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 [[Hydroxyl|hydroxy]] group to revert to a [[carbonyl]] group expelling the halide. Similar reactions involving any strong [[electronegative]] [[functional group]], such as a [[nitrile]], in place of the halide also occur. |
'''Geminal halide hydrolysis''' is an [[organic reaction]]. The reactants are a [[geminal]] [[halide|dihalide]] and [[water]] or a [[hydroxide]]. The reaction product is a [[ketone]] or an [[aldehyde]]. 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 [[Hydroxyl|hydroxy]] group to revert to a [[carbonyl]] group expelling the halide. Similar reactions involving any strong [[electronegative]] [[functional group]], such as a [[nitrile]], in place of the halide also occur. |
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== External links== |
== External links== |
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Revision as of 15:30, 16 August 2013
Geminal halide hydrolysis is an organic reaction. The reactants are a geminal dihalide and water or a hydroxide. The reaction product is a ketone or an aldehyde. 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 revert to a carbonyl group expelling the halide. Geminal trihalides (e.g. Benzotrichloride are first hydrolized to acid halides (e.g. Benzoyl Chloride) in a similar way and further to carboxylic acids. Similar reactions involving any strong electronegative functional group, such as a nitrile, in place of the halide also occur.
External links
- Benzophenone synthesis from benzene through benzophenone dichloride in Organic Syntheses Coll. Vol. 1, p.95; Vol. 8, p.26 Article
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