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NCERT Class XII Chemistry
Chapter - Aldehydes, Ketones and Carboxylic Acids
Questions with Solutions

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Question : 10
Total: 28
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:  
(i) It is given that the compound reduces Tollens’ reagent. This proves that the compound is an aldehyde. Further, the fact that it undergoes Cannizzaro reaction shows that it lacks an α-H atom.
(ii) On oxidation it yields 1,2-benzenedicarboxylicacid. This shows that it is an o-substituted benzaldehyde.
The only possible structure for the compound is :
The reactions undergone are :
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