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 aromatic compound .A. (MF `C_8H_8O)` gives positive 2,4-DNP test, it must be an aldehyde or a ketone.
(ii) Since compound .A. does not give Tollens. test or Fehling.s test, therefore, .A. must be a ketone.
(iii) Since compound .A. on treatment with `I_2//NaOH`, gives yellow ppt. of compound .B., therefore, compound .B. must be iodoform and the ketone .A. must be a methyl ketone.
(iv) Since methyl ketone .A. on drastic oxidation with `KMnO_4` gives a carboxylic acid .C. (M.F. `C_7H_6O_2)`, therefore, .C. must be benzoic acid and compound .A. must be acetophenone (`C_6H_5COCH_3)`.
(v) If .A. is acetophenone, then all the reactions described above may be explained as follows: