Mechanism of formation of 4-methyl- and 4-chloro-2-nitrophenol in the nitration of 4-methyl- and 4-chloro-anisole, respectively, in aqueous sulphuric acid
Abstract
The title reactions involve capture by water of the ipso-Wheland intermediates, followed by loss of methanol, then of nitronium ion to give solvent-caged ion pairs of para-substituted phenol and nitronium ion which can combine before or after diffusion apart.