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Question

An organic compound with molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen's reagent and undergoes Cannizaro reaction. On vigorous oxidation it gives a dicarboxylic acid which is used in the preparation of terylene. Identify the organic compound.

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Solution

The positive Brady's test (ie reaction with 2,4-dinitrophenylhydrazine) indicates that the organic compound is carbonyl compound and Tolllen's and Cannizoaro reactions indicate that it is an aldehyde without α-hydrogen atom. As the end product is terephthalic benzaldehyde
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