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) Resonance and the N≡N bond provide stabilization.
(b) The nitrogen lone pair forms a complex with Lewis acids, which deactivates the ring.
(c) Protonation yields -NH₃⁺, an electron-withdrawing group, promoting meta substitution.