PhOCH,C Nitriles CH H COOH cylated .-C=N can be hydrolyzed to carboxylic acid,so nitriles are acid derivatives. Nitrogen is sp hybridized,lone pair tightly held,so not very basic.(pK about 24). acetonitrile propyne Cnapter21 9 Chapter 21 9 Nitriles • -CN can be hydrolyzed to carboxylic acid, so nitriles are acid derivatives. • Nitrogen is sp hybridized, lone pair tightly held, so not very basic. (pKb about 24). =>