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Acyl chlorides are organic compounds containing the functional group -C(=O)Cl, with the general formula R-COCl, where R is a side chain.
Acyl chlorides are volatile fuming liquids that react with water to form hydrogen chloride and the carboxylic acid of the respective acyl chloride. Due to the Cl substituent, acyl chlorides do not form hydrogen bonds, which causes them to have have lower boiling and melting points than their corresponding carboxylic acid.
- RCOCl + H2O → RCO2H + HCl
Acyl chlorides can react with the salt of the corresponding carboxylic acid to give the anhydride of the said acid.
- CH3COCl + CH3COONa → (CH3CO)2O + NaCl
Due to their hazards, acyl chlorides are difficult if not impossible to get by the amateur chemist.
Acyl chlorides can be prepared by reacting a carboxylic acid or its salt with a chlorodehydrating agent, such as PCl3, PCl5 or SOCl2. Phosgene can also be used, but its great toxicity makes this route dangerous.
Acyl chlorides are corrosive and very toxic. Wear proper protection when working with them.