Question

Give plausible explanation for: 
(a) Diazonium salts of aromatic amines are stable.
(b) Aniline does not undergo Friedel-Crafts reaction. 
(c) Aniline on nitration gives substantial meta product.

Hint:

Basicity affects reactions!

Answer 1

(a) Stabilized by resonance and N≡N bond.
(b) Lone pair on nitrogen complexes with Lewis acid, deactivating the ring.
(c) Protonation makes -NH₃⁺, an EWG, favoring meta substitution.