Chapter  19: Carboxylic Acids

Reaction type : Nucleophilic Substitution then Nucleophilic Addition then  Nucleophilic Acyl Substitution !

Summary

• 1^o and 2^o alkyl halides (X = Cl, Br, I) or tosylates undergo S_N2 substitution with cyanide salts to give nitriles.
• Nitriles can be hydrolysed to carboxylic acids without the isolation of the amide intermediate.
• Note that the carbon skeleton is extended by 1 C atom during this reaction sequence.
• Although aromatic nitriles cannot be prepared via the S_N2 reaction, they too can be converted to the aromatic carboxylic acid by hydrolysis.

© Dr. Ian Hunt, Department of Chemistry, University of Calgary