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Question

An organic compound with the molecular formula C9H10O 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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Solution

An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative and also reduces Tollens reagent.
Hence, the compound is an aldehyde.
The compound undergoes Cannizzaro reaction. Hence, it does not contains an alpha H atom.
On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Hence, -CHO group is directly attached to benzene ring and the compound is ortho di-substituted benzene.
The compound.is 2-ethylbenzaldehyde.
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