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Home » Question 12.10: 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.
Question 12.10: 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.
Aldehydes, Ketones, and Carboxylic Acids | CBSE | Chemistry | Class 12 | Guides | NCERT
Question 12.10: 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.

Solution:

According to the question, the compound has molecular formula C9H10O and forms 2, 4-DNP derivative while also reducing Tollen’s reagent. Therefore, the given compound must be an aldehyde. Then, the compound forms 1, 2 benzene dicarboxylic acids and undergoes Cannizzaro reaction followed by oxidation. So, the −CHO group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted. Therefore, the compound is 2-ethylbenzaldehyde.

The reactions mentioned can be illustrated by the following equations.

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