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Preparation

The condensation of two carboxylic acid functions yields anhydrides.

Succinic acid dehydrates on heating to give succinic anhydride
Phthalic acid dehydrates on heating to give phthalic anhydride

The reaction is especially useful when it is intramolecularly carried out.

Click here to review the general addition-elimination mechanism of this reaction.

The preparation of mixed anhydrides, i.e. those produced from two different carboxylic acids, needs the previous activation of one of them. Otherwise, a mixture of three anhydrides would obviously be obtained.

Preparation of mixed anhydrides: a carboxylate attacks an acid chloride and chloride is released