Question

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 Tollens’ 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.

Answer 1

Identify the compound A

A $\left(C_8{H}_{8}O\right)$ gives a positive $2,4-DNP$ test, which shows that it contains a carbonyl group. It gives yellow precipitate with $I_2$ and $NaOH$ solution which shows that it has $-COC{H}_3$ group. It does not give Tollens or Fehling’s test which signifies that it is a ketone.