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.

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 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.,

MARKS App · Accepted Answer

Molecular formula of given aromatic compound is C 8 ​ H 8 ​ O . Possible structures of aromatic compound with molecular formula C 8 ​ H 8 ​ O are as follows. (i) (ii) (iii) (iv) (v) Since, 'A' does not give Tollen's and Fehling's test. Therefore it should be a ketone and not aldeh yde. So, (i) is the correct structure. The reactions involved are as following:

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