The acid-catalysed hydrolysis of acetanilide
Abstract
The rate of hydrolysis of acetanilide has been measured over a wide range of acidities in HCl, H2SO4, and HClO4, In H2SO4 80%(w/w) acetanilide undergoes sulphonation in preference to hydrolysis. Application of the Bunnett criteria of mechanism fit the data in HCl and H2SO4 well, whereas the data in HClO4 are fitted by an empirical two-term rate equation. A revised value of the constant –pKAH+ has been determined in each acid.