Question

please show work

Using the curved arrow formalism, draw the mechanism for the reaction between N-acetyl-ptoluidine with concentrated nitric acid. Be sure to show all of the intermediates and rationalize the regioselectivity of the reaction.

Answer 1

HCL 2 Cone. HNO3 - CH₂ with HCV N J CH3 N-acetyl-p-toluidine reach. ON 1 [product) Conc. HNO₃ is the source of No2 ion and this reaca goes through aromatie electrophilic substitution Yeae. Mechanism : chy He H3 AV NC Here, the - NHCOCH3 gr. is mild activating gr. so, wit Pulls e density from the ring but the or the position with respect to 'N-atom is slightly è rich than the meta position. So, nitration takes place only that or the position NO2 ANL NO2 11 from this it is observed that only the or the Positions doesn't CH3 Possess the charge and the para position + Босна бу methyl gr. and -CH3 soit No add to para position then aromaticity of the system will be lost so, only the above product is formed. CHZ 57