An aromatic compound (A), C_(7)H_(5)NO_(2)CI_(2) on reduction with Sn//HCI gives (G), which on reaction with NaNO_(2)//HCI gives (B). Compound (B) does not form a dye with beta-naphthol. However, (B) gives red colour with ceric ammonium nitrate and on oxidation gives an acid (D) of equivalent weight 191. Decarboxylation of (D) gives (E), which forms a mono nitro derivative (F) on nitrotion. Give the structures of (A) to (F) with proper reasoning.

An aromatic compound (A), C_(7)H_(5)NO_(2)CI_(2) on reduction with Sn/

1.	An aromatic compound (A), C_(7)H_(5)NO_(2)CI_(2) on reduction with Sn//HCI gives (G), which on reaction with NaNO_(2)//HCI gives (B). Compound (B) does not form a dye with beta-naphthol. However, (B) gives red colour with ceric ammonium nitrate and on oxidation gives an acid (D) of equivalent weight 191. Decarboxylation of (D) gives (E), which forms a mono nitro derivative (F) on nitrotion. Give the structures of (A) to (F) with proper reasoning.
Answer» SOLUTION :`DU in (A) `= ((2n_(C) + 2) - (n_(H) + n_(X) - n_(N)))/(2)` `= (16-(5+2-1))/(2)=5^(@)` `5^(@)` DU is due benzene (4 DU) and ONE `(---NO_(2))` group (1 DU)`. In (A), `(---NO_(2))` group cannot be with benzene ring, since reduction changes to `(---NH_(2))` ggroup, which on reaction with `(NaNO_(2) + HCI)` changes to alcohol. So it is in the side chain. Reactions: