An aromatic compound 'A' with the molecular formula C ₇ H ₇ NO ₂ on reduction with Sn/HCl gives compound 'B'. Compound 'B' upon treatment with NaNO ₂ /HCl at 273-278 K followed by warming with water gives compound 'C'. Compound 'C' reacts with bromine water to form a tribromo derivative. Identify compound 'A'.

Step-by-step solution

Compound 'A' ( C ₇ H ₇ NO ₂ ) is a nitrotoluene. Reduction of nitrotoluene with Sn/HCl yields a toluidine ('B'). Diazotization of toluidine followed by hydrolysis (warming with water) yields a cresol ('C'). For a cresol to form a tribromo derivative upon reaction with bromine water, all three positions ortho and para to the activating - OH group must be unsubstituted. In m -cresol (3-methylphenol), the - CH ₃ group is at the meta position, leaving both ortho positions and the para position free for electrophilic ar