An aromatic compound ‘A’ (Molecular formula C8H8O) gives positive 2, 4-DNP test. The compound gives a yellow precipitate of compound ‘B’ on treatment with iodine and sodium hydroxide solution. It d...

Question

An aromatic compound ‘A’ (Molecular formula C8H8O) gives positive 2, 4-DNP test. The compound gives a yellow precipitate of compound ‘B’ on treatment with iodine and sodium hydroxide solution. It does not give Tollen’s or Fehling’s test. On drastic oxidation with potassium permanganate it forms a carboxylic acid ‘C’ (Molecular formula C₇H₆O₂) which is also formed along with the yellow compound in the above reaction. Identify compounds A, B and C and write all the reactions involved.
OR

An organic compud ‘A’ (C₃H₄) on hyration in presence of H₂SO₄/HgSO₄ gives compound ‘B’ (C₃H₆O). Compound ‘B’ gives white crystalline product (D) with sodium hydrogensulphite. It gives negative Tollen’s test and positive iodoform’s test. On drastic oxidation ‘B’ gives compound ‘C’ (C₂H₄O₂) along with formic acid. Identify compounds ‘A’, ‘B’ and ‘C’ and explain all the reactions.

Philoid · Accepted Answer

The compound is Methyl Benzoate(A) which gives the 2,4 DNP test.

These are the compounds A, B, C with the following reactions.

OR

The reaction mechanism involves the following steps:

It is given that B gives negative tollents teat which means it is a Ketone.

The positive iodoform test suggest it has a structure similar to

Thus the compound B is propanone (common name acetone). It on the oxidation give acetic acid (compound C )and formic acid.