Question

An organic compound [A] `C_(8)H_(6)` on reacting with dilute sulphuric acid containing mercuric sulphate gives a compound [B] which can also be obtained from a reaction of bezene with acid chloride in the presence of anhydrous `AlCl_(3)`. The compound [B] when treated with iodine and aqueous NaOH yields [C] and a yellow compound [D]. Identify [A],[B],[C] and [D] with justification. Show how [B] is formed from [A].

Answer 1

(i) As the compound [B] can be formed by reacting benzene with acid chloride in the presence of anydrous `AlCl_(3)`, It is an aromatic ketone.
(ii) Since the compound [B] gives iodofrom [D] as one of the product on reacting iodine and aquoeus `NaOH`, the compound [B] is acetophenone.
(iii) The compound [A] seems to be a derivative of acetylene since it undergoes hydration under acidic conditions to form [B] which is a ketone i.e., acetophenone.
The sequence may be shown as follows: