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  • An aromatic compound ‘A’ (Molecular formula CgHgO) 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

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 reactions involved.

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Molecular formula of the compound in question is C_{8}H_{8}O. It is given that ‘A’ does not give Tollens’ or Fehling’s test, making it a ketone. Since we get  positive test with 2, 4-DNP and iodoform test, It means it is methyl ketone.



 

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