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Chapter 19: Carboxylic Acids
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Hydrolysis of Nitriles
Reaction type : Nucleophilic Substitution then Nucleophilic
Addition then Nucleophilic Acyl Substitution !
Summary
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1o and 2o alkyl halides
(X = Cl, Br, I) or tosylates undergo
SN2 substitution with cyanide salts to
give nitriles.
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Nitriles can be hydrolysed to carboxylic acids without the isolation of
the amide intermediate.
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Note that the carbon skeleton is extended by 1 C atom during this reaction
sequence.
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Although aromatic nitriles cannot be prepared via the SN2 reaction, they
too can be converted to the aromatic carboxylic acid by hydrolysis.
