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An aromatic compound 'A' (Molecular form...

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.

Text Solution

Verified by Experts

Since the aromatic compound 'A' does not give Tollen's reagent test or Fehling's test, it is not an aromatic aldehyde. As it respond to iodoform test, it is a methylketone. The series of reactions involved are listed.
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