Rearrangement of N-Chlorobenzanilide

Department of Chemistry, Government Postgraduate College, Shivpuri, M.P. Manuscript received 28 May 1981, accepted 4 August 1981 Rates for rearrangement of N-chlorobenzanilide increase with increase in acid concentration in the range 0.5 to 3.0 M hydrochloric and sulphuric acids. The reaction is first order with respect to substrate concentration, H+ ion concentration and is photochemically sensitive. Overall reaction is governed by acid catalysed rates except at ionic strength 1.5\(\mu\). Bunnett and Bunnett-Olsen plot data show dependence of rates on water activity. Formation of benzoic acid from hydrolysis of N-chlorobenzanilide shows that chlorine does not migrate to this part of the molecule