Answer :

compound A is obviously is a ketone because it gives positive 2,4- DNP and positive iodoform test but does not respond to Tollen’s or Felling’s solution ( not aldehyde).

With the molecular formula of C8H8O and D.B.E. calculation of : 8 (carbon no.s) –(8/2) (hydrogens no./2) +0 (no nitrogen) +1 = 5, therefore it has 5 unsaturations in forms of the ring or double bonds or both.

Hence the structure of A should be :

i.e. acetophenone, justified by the 4 double bonds, 1 ring, and one carbonyl carbon.

It gives positive 2,4-DNP test :

It gives a positive iodoform test:

‘B’ (yellow ppt)

Hence the yellow compound formed on iodoform reaction is CHI3.

On drastic oxidation with potassium permanganate, it forms a carboxylic acid ‘C’ which is actually benzoic acid which is formed from acetophenone.

structure of ‘C’

The reaction is as follows :

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