o -Anisidine undergoes the following sequence of reactions: o -Anisidine Br ₂ (aq) A NaNO ₂ / HCl, 273-278 K B CH ₃ CH ₂ OH, C The final major product C is:

Step-by-step solution

o -anisidine (2-methoxyaniline) has two activating groups: - NH ₂ and - OCH ₃ . The - NH ₂ group is much more strongly activating and controls the orientation of electrophilic aromatic substitution. Reaction with aqueous bromine leads to exhaustive bromination at the available ortho and para positions with respect to the - NH ₂ group. Since one ortho position is occupied by the - OCH ₃ group, bromination occurs at positions 4 and 6, yielding 4,6-dibromo-2-methoxyaniline (Compound A). Treatment with NaNO ₂ and HCl a