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.
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
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.
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\((v)\)
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Concepts Used:
Aldehydes, Ketones and Carboxylic Acids - Chemical Reactions
Chemical Reactions of Aldehydes and Ketones:
- Cross aldol condensation
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