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An organic compound [A] C(8)H(6) on reac...

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 benzene 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]`.

Text Solution

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(i) As the compound `[B]` can be formed by reacting benzene with acid chloride in the presence of anhydrous `AlCl_(3)`, it is an aromatic ketone.
(ii) Since the compound `[B]` gives iodoform `[D]` as one of the product on reacting iodine and aqueous `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 :
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