0 PhOCH,C- NH CH Nitriles CH3 COOH acylated. mnactive .-C=N can be hydrolyzed to carboxylic enzyme acid,so nitriles are acid derivatives. Nitrogen is sp hybridized,lone pair tightly held,so not very basic(pKp about 24) 3> acetonitrile propyne Chapter 21 10Chapter 21 10 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). =>