Rearrangement of N-Chloroanilides in Aqueous Media

Department of Chemistry, Government Post.Graduate College, Shivpuri, M.P. Manuscript received 15 May 1975, revised 11 March 1976, accepted 1 September 1976 Rates for the rearrangement of N-Chloroacetanilide and its o-Chloro derivative in hydra chloric and sulphuric acids increase with increase in acid concentration, however, with change in buffer concentration no appreciable difference of rates has been observed. Constant ionic strength effect data shows that reaction is subject to positive salt effect, involves both acid catalysed and neutral rearrangements and that substitution of chlorine brings no change on the effectiveness of acid catalysis. The sum of calculated acid and neutral rates for rearrangement from ionic strength effect data using second empirical term of Debye-Huckel equation do not agree with experimental rates uniformly over the whole range of acidity. Bunnett and Bunnett-Olsen plot data, Zucker Hammett hypothesis show that reaction is bimolecular and involves a nucleophilic attack of water in rate determining step