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An organic compound with the molecular formula \(\mathrm{C}_9 \mathrm{H}_{10} \mathrm{O}\) forms 2, 4-DNP derivative, reduces Tollen's reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the compound.
ChemistryAldehydes, Ketones and Carboxylic Acids
Solution:
1119 Upvotes Verified Answer
Since the given compound with molecular formula \(\mathrm{C}_9 \mathrm{H}_{10} \mathrm{O}\) forms a 2, 4-DNP derivative and reduces Tollen's reagent, it must be an aldehyde. Since it undergoes Cannizzaro reaction, therefore, \(\mathrm{CHO}\) group is directly attached to the benzene ring.
Since on vigorous oxidation, it gives 1, 2-benzene dicarboxylic acid, therefore, it must be an ortho-substituted benzaldehyde. The only \(o\)-substituted aromatic aldehyde having molecular formula \(\mathrm{C}_9 \mathrm{H}_{10} \mathrm{O}\) is \(o\)-ethyl benzaldehyde. All the reactions can now be explained on the basis of this structure.

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