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An organic compound with the molecular formula C_(9)H_(10)O forms 2, 4 - DNP derivative, reduces Tollens' reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2 - benzenedicarboxylic acid. Identify the compound. |
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Answer» Solution :(i) Since the given compound FORMS a 2, 4 - DNP derivative and reduces TOLLENS. reagent, it must be an aldehyde. As the molecular formula is `C_(9)H_(10)O`, this is PROBABLY an aromatic compound. (ii) Since it undergoes Cannizzaro reaction, THEREFORE, `CHO` group is directly attached to the benzene ring. (iii) On vigorous oxidation, it gives 1, 2 - benzenedicarboxylic acid, therefore, it must be an ortho substituted benzaldehyde. The only o - substituted aromatic aldehyde having molecular formula `C_(9)H_(10)O` is 2 - ethylbenzaldehyde. Al the reaction can now be explained on the basis of this structure. 
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