Question

An aromatic compound 'A' (Molecular formula C₈H₈O) 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 Tollens' or Fehling's test. On drastic oxidation with potassium permanganate it form a carboxylic acid 'C' (Molecular formula C₇H₆O₂), which is also formed along with the yellow compound in the above reaction. Identify A, B and C and write all reactions involve.

Answer 1

Molecular formula of compound is C₈H₈O. As 'A' does not give Tollens' or Fehling's test. It must be a ketone. It gives positive test with 2,4-DNP and iodoform test. It means it is methyal ketone.