Question
An organic compound with molecular formula $C _9 H _{10} O$ forms 2,4-DNP derivative, reduces Tollen's reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.
✓
Answer
(i) The given compound with molecular formula $C _9 H _{10} O$ forms a 2, 4-DNP derivative and reduces Tollen's reagent, it must be an aldehyde.
(ii) As it undergoes Cannizzaro reaction, therefore, CHO group is directly attached to the benzene ring.
(iii) In vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid, therefore, it must be an ortho-substituted benzaldehyde. The only $o$-substituted aromatic aldehyde having molecular formula $C _9 H _{10} O$ is o-ethylbenzaldehyde. All the reactions can be explained on the basis of this structure.
(ii) As it undergoes Cannizzaro reaction, therefore, CHO group is directly attached to the benzene ring.
(iii) In vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid, therefore, it must be an ortho-substituted benzaldehyde. The only $o$-substituted aromatic aldehyde having molecular formula $C _9 H _{10} O$ is o-ethylbenzaldehyde. All the reactions can be explained on the basis of this structure.
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