Chemistry · Ch 11 — Hydroxy Compounds and Ethers
Reaction of Phenol with Ammonia
11.15.2
Reaction of Phenol with Ammonia
Phenol heated with ammonia in the presence of anhydrous ZnCl2 undergoes nucleophilic replacement of -OH by -NH2 to give aniline: C6H5-OH + NH3 (anhydrous ZnCl2) gives C6H5-NH2 + H2O. The anhydrous ZnCl2 acts as a Lewis-acid catalyst, coordinating to phenol's oxygen and making the ring carbon a better site for the incoming ammonia nucleophile; this reaction, run in reverse of section 11.13.3's diazotisation r …