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In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
Strictly speaking, this reaction results in the formation of a rhodium carbonyl complex rather than free carbon monoxide. The catalytic cycle is assumed to involve oxidative addition of the aldehyde (or acid chloride) to gives a 16e acyl Rh(III)-hydride intermediate, which undergoes migratory extrusion of CO proceed to form an 18-electron d6 Rh ...
In the IUPAC nomenclature of organic chemistry, the systematic names of acyl groups are derived exactly by replacing the -yl suffix of the corresponding hydrocarbyl group's systemic name (or the -oic acid suffix of the corresponding carboxylic acid's systemic name) with -oyl, as shown in the table below.
The Blaise ketone synthesis (named after Edmond Blaise) is the chemical reaction of acid chlorides with organozinc compounds to give ketones.. The Blaise ketone synthesis. The reaction was claimed to bring excellent yields by Blaise, however, investigators failed to obtain better than moderate yields (50%).
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Acyl halides and acid anhydrides of carboxylic acids are also common acylating agents. In some cases, active esters exhibit comparable reactivity. All react with amines to form amides and with alcohols to form esters by nucleophilic acyl substitution. Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation.