An organic compound 1-ethyl-2-nitrobenzene is subjected to the following sequence of reactions: (i) Br ₂ / FeBr ₃ (ii) Sn / HCl (iii) NaNO ₂ / HCl , 273-278 K (iv) CH ₃ CH ₂ OH (v) KMnO ₄ / KOH , followed by H ₃ O ^+ Identify the structure of the final major product.

Step-by-step solution

In 1-ethyl-2-nitrobenzene, the - CH ₂ CH ₃ group is activating and ortho/para-directing, while the - NO ₂ group is deactivating and meta-directing. Both groups reinforce electrophilic attack at the position para to the ethyl group (position 4). Step (i): Bromination yields 4-bromo-1-ethyl-2-nitrobenzene as the major product. Steps (ii) and (iii): Reduction with Sn / HCl converts the - NO ₂ group to - NH ₂ , which is then diazotized by NaNO ₂/ HCl to form a diazonium salt ( - N ₂^+ Cl ^- ). Step (iv): Ethanol ( CH ₃