Consider the following sequence of reactions starting from 4-methylaniline: 4-Methylaniline (i) Ac ₂ O / Pyridine P (ii) Br ₂ / CH ₃ COOH Q (iii) H ₃ O ⁺ R R (iv) NaNO ₂ / HCl , , 0-5^ C then H ₃ PO ₂ S (v) Mg / dry ether then CO ₂ / H ₃ O ⁺ T The major product 'T' is:

Step-by-step solution

Step (i): 4-Methylaniline reacts with acetic anhydride in the presence of pyridine to form N-(4-methylphenyl)acetamide (compound P). This step protects the highly reactive - NH ₂ group. Step (ii): Bromination of P with Br ₂ in acetic acid. The - NHCOCH ₃ group is ortho/para directing and is a stronger activator than the - CH ₃ group. Since the para position is blocked by the methyl group, bromination occurs ortho to the - NHCOCH ₃ group, yielding 2-bromo-4-methylacetanilide (compound Q). Step (iii): Acidic hydrolys