An organic compound (A) of molecular weight 135 on boiling with NaOH evolves a gas which gives dense white fumes on bringing a rod dipped in HCl near it. The alkaline solution thus obtained on acidification gives the precipitate of a compound (B), having molecular weight 136. Treatment of (A) with HNO2 also yields (B), whereas its treatment with Br2 / KOH gives (C). Compound (C) reacts with cold HNO2 to give (D) which gives red colour with ceric ammonium nitrate. On the other hand, (E) an isomer of (A) on boiling with dilute HCl gives an acid (F), having molecular weight 136. On oxidation, followed by heating, (F) gives an anhydride (G) which condenses with benzene in the presence of AlCl3 to give anthraquinone, Give structures of (A) to (G) with proper reasoning.
