An organic compound (A) with molecular formula `C_8H_8 O` forms an orange red precipitate with 2,4 -DNP reagent and gives yellow precipitate on heating with iodine in the presence of sodium hydroxide . It neither reduces Tollen's reagent or Fehling's solution , nor does it decolourise bromine water or Baeyer's reagent. On drastic oxidation with chromic acid, it gives a carboxylic acid (B) having molecular formulae `C_7H_6O_2`. Identify the compound (A) and (B) and explain the reactions involved .

Options

A.
B.
C.
D.

Answer

A

Explanation

X form `2, 4`-DNP derivative so it is an aldehyde or ketone, X must be ketone as it does not reduce Tollen's or Fehilling reagent. X must be methyl ketone as it responds to iodoform test. X do not decolourise bromined water which suggests the presence of unsaturation due to an aromatic ring.
Compound Y should be benzoic acid according to the molecular formula of Y. The compound X must be monosubstituted aromatic methyl ketone.
Compound X is phenylmethyl ketone.