Question

An organic compound (A) of molecular weight 135, on boiling with NaOH evolves a gas which gives white dense 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 gives (D), which give red colour with ceric ammaonium 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 anhydrous AlCl₃ to give anthraquinone. Give the structures of (A) to (G) with proper reasoning.

Answer 1

 ∴ NH⁺₄ as gas is NH₃

B = C₇ H₅ NH₂ Cl₂ does not give compound B-does not form a dye with β -naphthol 

∴ A is (C) is a primary alcohol. as de-carboxylation gives single derivatives 

∴ Cl should be symmetrically oppositely placed.