An aromatic compound ‘A’ (Molecular formula [\ce{C8H8O}]) gives positive 2, 4-DNP test. It gives a yellow precipitate of compound ‘B’ on treatment with iodine and sodium hydroxide soluti

Question

An aromatic compound ‘A’ (Molecular formula \[\ce{C8H8O}\]) 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 Tollen’s or Fehling’s test. On drastic oxidation with potassium permanganate it forms a carboxylic acid ‘C’ (Molecular formula \[\ce{C7H6O2}\]), which is also formed along with the yellow compound in the above reaction. Identify A, B and C and write all the reactions involved.

Long Answer

Solution

Molecular formula of compound is \[\ce{C8HgO}\]. 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 methyl ketone.