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.

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.

cdquestions Admin · Accepted 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 ortho-substituted.Hence,the compound is  $2-ethylbenzaldehyde.$ The given reactions can be explained by the following equations.

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.

Solution and Explanation

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