ACID HALIDE THEORY

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ACID HALIDE THEORY
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IUPAC names alkanoyl halides by replacing the ending -oico of the acid with the same number of carbons per -oilo. In addition, the word acid is replaced by the corresponding halogen, named as salt.

nomenclature-alkanoyl-halides-01.gif

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ACID HALIDE THEORY
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Alkanoyl halides react with water at room temperature to form carboxylic acids.

hydrolysis-halides-alkanoyl

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ACID HALIDE THEORY
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The reaction of alkanoyl halides with alcohols produces esters. The equilibria of this reaction are favored by eliminating the hydrochloric acid with a base (tertiary amine, pyridine)

reaction-halides-alkanoyl-alcohols

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ACID HALIDE THEORY
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Amines and ammonia react with alkanoyl halides to form amides. The reaction is favored with an excess of amine, in order to eliminate the hydrochloric acid released in the reaction.

 
reaction-halides-alkanoyl-amides

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ACID HALIDE THEORY
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Magnesium organometallics at -78°C react with alkanoyl halides to form ketones. It is necessary to work at a low temperature to avoid adding a second equivalent of organometallic, in which case the product obtained would be an alcohol.

 
reaction-alkanoyl-organometallic-halides

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ACID HALIDE THEORY
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Alkanoyl halides are reduced to alcohols with the lithium aluminum reductant

 
reduction-halides-alcohols

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ACID HALIDE THEORY
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The reduction of alkanoyl halides can be stopped at the aldehyde using modified hydrides. From lithium aluminum hydride lithium tri(tert-butoxy)aluminum hydride can be prepared. This modified hydride allows reduction of acid halides to aldehydes.

 
Synthesis of the reductant: the reductant is obtained by reaction between lithium aluminum hydride and tert-butanol
 
reduction-halides-aldehydes

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ACID HALIDE THEORY
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Alkanoyl halides are reduced to aldehydes with hydrogen and a palladium poisoned catalyst.

reduction-rosenmund