Question
An organic compound with the molecular formula $C_9H_{10}O$ forms $2,4-DNP$ derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives $1, 2-$benzenedicarboxylic acid. Identify the compound.
✓
Answer
It is given that the compound $($with molecular formula $C_9H_{10}O)$ forms $2, 4-DNP$ derivative and reduces Tollen's reagent. Therefore, the given compound must be an aldehyde. Again, the compound undergoes cannizzaro reaction and on oxidation gives $1, 2-$ benzenedicarboxylic acid. Therefore, the $-CHO$ group is directly attached to a benzene ring and this benzaldehyde is or tho-substituted. Hence, the compound is $2-$ethylbenzaldehyde.
The given reactions can be explained by the following equations.
The given reactions can be explained by the following equations.
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