Answer to Question #136714 in Organic Chemistry for Muqadas cheema

Question

Why Aniline is stronger base than Trinitro Aniline?

Answer 1

basicity means the ability of donating electron pair,now aniline has 1 lone pair on the N atom of NH2 group,which is stabilized by resonance in the benzene ring. So,the availability of the lone pair is less.

on the other hand, p-nitroaniline has an electron withdrawing group in the para position and due to these EWG the lone pair of NH2 is more stabilized by resonance and availability of the lone pair becomes less than that of aniline.

that's why aniline is more basic than p-nitro aniline.