An organic compound with the molecular formula C_9H_ 10 O forms 2… - Vidyadip

Question

An organic compound with the molecular formula $\ce{C_9H_{10}O}$ forms $2,4-\ce{DNP}$ 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 $\ce{C_9H_{10}O)}$ forms $2, 4-\ce{DNP}$ 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 $-\ce{CHO}$ 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.

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