Identify the major product of the following reaction sequence: (i) Ac ₂ O (ii) HNO ₃, H ₂ SO ₄ (iii) H ₃ O ⁺ (iv) Br ₂ + NaHCO ₃ (v) NaNO ₂ + HCl (vi) H ₃ PO ₂ (vii) Fe + HCl (viii) OH ⁻ / H ₂ O

Step-by-step solution

Reaction of aniline with Ac₂O yields acetanilide, protecting the amino group and reducing its activating effect. Nitration of acetanilide with HNO₃ and H₂SO₄ gives p-nitroacetanilide as the major product due to steric hindrance at the ortho position. Acidic hydrolysis using H₃O^+ removes the acetyl group to yield p-nitroaniline. Bromination with Br₂ and NaHCO₃ substitutes bromine at both ortho positions relative to the strongly activating -NH₂ group, forming 2,6-dibromo-4-nitroaniline. Reaction with NaNO₂ and HCl c