Question

 An organic compound A, (C₈H₆) on treatment with dilute sulphuric acid containing mercuric sulpharie gives a compound B, which can also be obtained from a reaction of benzene with an acid chloride in the presence of anhydrous aluminium chloride. The compound B, when treated with iodine in aqueous KOH, yields C and a yellow compound D. ldentify A, B, C and D with justification. Show how B is formed from A?

Answer 1

Compound D is iodoform which is formed with compound B by the reaction of I₂ in presence of KOH (ie Iodoform reaction). Hence, compound B must have CH₃-CO-group.

Compound B is obtained by the reaction of an acid chloride with benzene in presence of anhydrous AlCl₃. So, compound B is C₆H₅COCl.

Hence,

It is also obtained with compound A by the reaction with dil. H₂SO₄ in presence of HgSO_4. So, compound A is

Compound B gives iodoform test with I₂, and KOH(aq)