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' tratment with iodine and sodium hydroxide solution. Compound 'A' does not gives Tollen' or Fehling test on drastic oxidation with potassiium permaganate it forms a carboxylic acid 'C' (Molecular formula $C_{7} H_{6} O_{2}$ ), which is also formed along with the yellow compound in the above reaction. Identify A, B and C and write all the reactions involved.

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Solution

Molecular formula = $C_{8} H_{8} O$
Degree of unsaturation = $(C_{n} + 1) - \frac{H_{n}}{2} = (8 + 1) - \frac{8}{2} = 9 - 4 = 5$
Degree of unsaturation > 5 i.e., it may contain benzene ring having degree of unsaturation equal to 4 and one fegree of unsatration ,ust bee carbonyl group

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