Which of the following reaction sequences is most suitable for the synthesis of 3,5-dibromotoluene from p -toluidine?

Step-by-step solution

To synthesize 3,5-dibromotoluene from p -toluidine (4-methylaniline), we need to introduce two bromine atoms meta to the methyl group. Direct bromination of toluene would yield ortho and para products, so the directing effect of the - NH ₂ group must be utilized before it is removed. Step (i): Reaction of p -toluidine with bromine water ( Br ₂( aq ) ) leads to polybromination because the - NH ₂ group is highly activating. Bromine atoms are added to both available ortho positions relative to the - NH ₂ group, yieldi