(a) Account for the following :
(i) Direct nitration of aniline yields significant amount of meta derivative.
(ii) Primary aromatic cannot be prepared by Gabriel phthalimide synthesis.
(b) Carry out the following conversions :
(i) Ethanoic acid into methanamine.
(ii) Aniline to p-Bromoniline.
(c) Arrange the following in increasing order of basic strength :
Aniline, p-nitroaniline and p-toludine.

Explanation

(a) (i) In strongly acidic medium, aniline is protonated to form the anilium ion which is meta directing.
(ii) Aryl halidas do not undergo nucleophilic substitution with the anion formed by phthalimide.
(b) (i) `CH_(3)-COOH overset(NH_(3),Delta)(to) CH_(3)-CO-NH_(2) overset(NaOH + Br_(2))(to) CH_(3)NH_(2)`
(ii)

(c) `"p-Nitroaniline" lt "Aniline" lt "p-Toludine".`