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 permanganate, 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.

Explanation

Molecular formula `=C_(8)H_(8)O`
Degree of unsaturation `=(C_(n)+1)-(H_(n))/(2)`
`=(8+1)-(8)/(2)=9-4=5`
Degree of unsaturation `gt5` i.e., it may contain benzene ring having degree of unsaturation equal to 4 and one degree of unsaturation must be carbonyl group.
Thus, possible structures are

According to question, compound 'A' does not respond to Tollen's or Fehling's test, So, it is a ketone not aldehyde. Therefore, structure, I is correct. Complete reaction sequence is as follows