(a)(i) Draw the zwitterion structure of sulphanilic acid.
(ii) How can the activating effect of the –NH₂ group in aniline be controlled?
(ii) How can the activating effect of the –NH₂ group in aniline be controlled?
Answer: (i) p-H₃N⁺–C₆H₄–SO₃⁻. (ii) By acetylation (protecting –NH₂ as –NHCOCH₃), which withdraws the lone pair toward C=O.
Solution
(i) The basic –NH and acidic –SOH neutralise each other internally:
(ii) Acetylate the amine to acetanilide: the lone pair now conjugates with the acetyl C=O, moderating ring activation — mono-substitution becomes controllable; the amide is hydrolysed back afterwards.
(ii) Acetylate the amine to acetanilide: the lone pair now conjugates with the acetyl C=O, moderating ring activation — mono-substitution becomes controllable; the amide is hydrolysed back afterwards.
CBSE Class 12 Board · 2023 · Subjective