An isomeric toluidine (methylaniline) undergoes the following sequence of reactions: (i) Br ₂ / H ₂ O (ii) NaNO ₂ / HCl , 0^ C (iii) H ₃ PO ₂, H ₂ O If the final major product obtained is 2,4,6-tribromotoluene, the starting aromatic amine is:

Step-by-step solution

The final product is 2,4,6-tribromotoluene, which means three bromine atoms are at positions 2, 4, and 6 relative to the methyl group. The reaction sequence involves: 1. Polybromination of an activated ring (directed by the - NH ₂ group to its ortho and para positions). 2. Diazotization of the - NH ₂ group to - N ₂^+ Cl ^- . 3. Reduction (deamination) of the diazonium salt by H ₃ PO ₂ , replacing the diazonium group with a hydrogen atom. To yield 2,4,6-tribromotoluene, the original - NH ₂ group must have been locat