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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.

Q 12.10     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-benzene dicarboxylic acid. Identify the compound.

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M manish

According to given information, the molecular formula is C_{9}H_{10}O and it reduces tollens reagent. So, there must be an aldehyde group.And also it gives cannizaro reaction, it means the given copound has no \alpha-hydrogen atom. On oxidation it gives 1,2-benzenedicarboxylic acid. Thus, the aldehyde group (-CHO) is directly attached with the benzene ring and also it should be para-substituted.

Hence, the structure of the compound (2-ethyl benzaldehyde) is-

By following reaction we can undrstand this prblem-

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