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Hydrolysis of Nitriles to Carboxylic Acids

OCR A-level Organic ChemistryCarbon-Carbon Bond FormationLesson 5 of 8

A nitrile can also be converted into a carboxylic acid by hydrolysis, a reaction in which water breaks bonds in the molecule.

OCR's conditions are to heat the nitrile with dilute aqueous acid, for example dilute hydrochloric acid, HCl(aq). The C≡N group becomes a −COOH group and the nitrogen is released as an ammonium ion:

R−CN + 2H2O + H+ → R−COOH + NH4+

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Key terms in this lesson

nitrile
A compound containing the -C≡N functional group, often made by reacting a haloalkane with cyanide ions.

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