An aromatic compound 'A' (molecular formula `C_(8)H_(8)O`) gives positive 2, 4-DNP test. It gives a yellow precipitate of compound 'B' on treatment with iodine and sodium hydroxide solution. Compound 'A' does not give Tollen's or Fehling's test. On drastic oxidation with potassium permaganate it forms a carboxylic acid 'C' (molecular formula `C_(7)H_(6)O_(2)`), which is also formed alongwith the yellow compound in the above reaction. Identify A, B and C and write all the reactions involved.

Explanation

(i) Since the compound [A] gives positive DNP and iodoform tests, it must have a methyl ketonic group `(CH_(3)-CO-)`.
(ii) Since the compound [A] does not reduce Tollen's reagent or Fehling solution, it is not an aldehyde.
(iii) As the compound [A] does not decolourise bromine water, it must be saturated in nature and is expected to be an aromatic compound.
(iv) The avialable infomation shows that the compound [A] upon oxidation with chromic acid `[H_(2)CrO_(4)]` gives carboxylic acid [B] with molecular formula `C_(7)H_(6)O_(2)`. The formula is of benzoic acid which is an aromatic acid.
(v) Since [B] has been formed as a result of oxidation of compound [A], this shows that the compound which is a methyl ketone has the formula `C_(6)H_(5)-overset(O)overset(||)C-CH_(3) (C_(8)H_(8)O)` and is acetophenone.
The reaction involved are as follows: