An organic compound containing (x) with molecular formula `C_(8)H_(8)O` forms an oragne-red precipitate with `2,-`-DNP reagent and gives yellow precipitate on heating with ioxdine in the presence of sodium hydroxide.
It neither reduces Tollen's Fehlling's reagent, nor does it decolouries bromine water or Baeyer's reagent.
On drastic oxidation with chromic acid, it gives a carboxylic acid (Y) having molcular formula `C_(7)H_(6)O_(2)`. Identify the compounds X and Y.

Explanation

(A) forms 2,4-DNP derivative. Therefore, it is an aldehyde or a ketone. Since it does not reduce Tollens’ or Fehling reagent, (A) must be a ketone. (A) responds to iodoform test. Therefore, it should be a methyl ketone. The molecular formula of (A) indicates high degree of unsaturation, yet it does not decolourise bromine water or Baeyer’s reagent. This indicates the presence of unsaturation due to an aromatic ring.
Compound (B), being an oxidation product of a ketone should be a carboxylic acid. The molecular formula of (B) indicates that it should be benzoic acid and compound (A) should, therefore, be a monosubstituted aromatic methyl ketone. The molecular formula of (A) indicates that it should be phenyl methyl ketone (acetophenone). Reactions are as follows: