Consider the following reaction sequence starting with p -nitrotoluene: p -nitrotoluene (i) Br ₂ , Fe (ii) Sn, HCl (iii) NaNO ₂ , HCl, 273 K (iv) H ₃ PO ₂ , H ₂ O (v) KMnO ₄ , H ^+ , Major Product The major final organic product formed is:

Step-by-step solution

In p -nitrotoluene, the - CH ₃ group is activating and ortho/para-directing, while the - NO ₂ group is deactivating and meta-directing. Both groups synergistically direct the incoming electrophile ( Br ^+ ) to the position ortho to the - CH ₃ group. Thus, bromination yields 2-bromo-4-nitrotoluene. Reduction with Sn/HCl converts the - NO ₂ group to an - NH ₂ group, forming 4-amino-2-bromotoluene. Reaction with NaNO ₂ /HCl at 273 K diazotizes the amine to form 3-bromo-4-methylbenzenediazonium chloride. Treatment with