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

(1) Positive DNP test and +ve iodoform test suggests that it is a carbonyl compound containing `CH_(3)-overset(O)overset(||)C-` group but `-ve` Tollen's and Fehling's tests suggest that it must be a methyl ketone and not an aldehyde.
(2) Molecular formula of compound A shows high degree of unsaturation but as it does not decolourless to `Br_(2)` water and Bayer's reagent, it must not be an aliphatic alkene, rather it must include an aromatic ring also.
(3) Thus compound A can be
Let us try all the reactions involved in the question.