Benzene on reaction with HOCl in presence of an acid produces organic compound (A). (A) on treatment with NaNH_(2)//liq." "NH_(3) furnishes another organic compound (B). (B) on treatment with HBF_(4) affords an organic compound (C) which on heating with NaNO_(2) gives organic compound (D). Identify (A), (B), (C) and (D).

Benzene on reaction with HOCl in presence of an acid produces organic

1.	Benzene on reaction with HOCl in presence of an acid produces organic compound (A). (A) on treatment with NaNH_(2)//liq." "NH_(3) furnishes another organic compound (B). (B) on treatment with HBF_(4) affords an organic compound (C) which on heating with NaNO_(2) gives organic compound (D). Identify (A), (B), (C) and (D).
Answer» Solution :(i) `HOCl` in presence of an acid generates the reactive electrophile, chloronium ION `(Cl^(+))` which attacks benzene to give chlorobenzene (A). (ii) Chlorobenzene (A) on treatment with `NaNH_(2)//liq." "NH_(3)` undergoes dehydrohalogenation via benzyne to afford aniline (B). (iii) Aniline (B) on treatment with `HBF_(4)` forms the CORRESPONDING salt anilinium tetrafluoroborate (C) which on HEATING with `NaNO_(2)` undergoes Balz-Schiemann reaction through the intermedium formation of benzenediazonium tetrafluoroborate to affford FLUOROBENZENE (D). .