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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.
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
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.
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid: [8] C 6 H 5 CCl 3 + H 2 O → C 6 H 5 COCl + 2 HCl C 6 H 5 CCl 3 + C 6 H 5 CO 2 H → 2 C 6 H 5 COCl + HCl. As with other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride or thionyl chloride.
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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.
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The acyl azide is usually made from the reaction of acid chlorides or anhydrides [6] with sodium azide [7] or trimethylsilyl azide. [8] Acyl azides are also obtained from treating acylhydrazines with nitrous acid. [9] Alternatively, the acyl azide can be formed by the direct reaction of a carboxylic acid with diphenylphosphoryl azide (DPPA ...