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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 is a reagent for the preparation of esters and amides of acetic acid, used in the derivatization of alcohols and amines. One class of acetylation reactions are esterification, for example the reaction with ethanol to produce ethyl acetate and hydrogen chloride: CH 3 COCl + HO−CH 2 −CH 3 → CH 3 −COO−CH 2 −CH 3 + HCl
As originally determined by Staudinger, [7] oxalyl chloride reacts with water giving off gaseous products only: hydrogen chloride (HCl), carbon dioxide (CO 2), and carbon monoxide (CO). [9] (COCl) 2 + H 2 O → 2 HCl + CO 2 + CO. Other acyl chlorides hydrolyze with formation of hydrogen chloride and the original carboxylic acid.
Water conditioners are formulations designed to be added to tap water before its use in an aquarium. [1] [2] If the tap water is chlorinated then a simple conditioner containing a dechlorinator may be used. These products contain sodium thiosulfate which reduces chlorine to chloride which is less harmful to fish.
However, for certain reactive acyl chlorides the activity must be reduced further, by the addition of a poison. Originally this was thioquinanthrene although thiourea [ 2 ] has also been used. [ 3 ] [ 4 ] Deactivation is required because the system must reduce the acyl chloride but not the subsequent aldehyde.
Weak bases are better leaving groups than strong bases; a species with a strong conjugate acid (e.g. hydrochloric acid) will be a better leaving group than a species with a weak conjugate acid (e.g. acetic acid). Thus, chloride ion is a better leaving group than acetate ion. The reactivity of acyl compounds towards nucleophiles decreases as the ...
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.
This page was last edited on 28 October 2023, at 00:03 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
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