Question

An organic compound with the molecular formula C₉H₁₀O forms 2,4-DNP derivative, reduces Tollens it gives 1,2-benzenedicarboxylic acid. Identify the compound.

Answer 1

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Q.) An organic compound with the molecular formula C₉H₁₀O forms 2,4-DNP derivative, reduces Tollens it gives 1,2-benzenedicarboxylic acid. Identify the compound ?

Ans.) Given , that the compound (with molecular formula C9H10O) forms 2, 4-DNP derivative and reduces Tollen's reagent.
.-. , the given compound must be an aldehyde.
Again, the compound undergoes cannizzaro reaction and on further oxidation gives 1, 2-benzenedicarboxylic acid. Therefore, the -CHO group is directly attached to a benzene ring ( C6H5 ) and this benzaldehyde is ortho-substituted. Hence, the compound we got is 2-ethylbenzaldehyde .

And , Refer The Attachment .

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Answer 2

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( 1 ). since the given compound with Molecular formula $\bold{C_9H_{10}O}$forms 2,4 -DNP derivative and reduces tollen's reagent it must an aldehyde.

( 2 ). since it undergoes Cannizzaro reaction therefore, CHO group is directly attached to benzene ring.

( 3 ). Since Vigorous Oxidation It Gives 1,2-benzenedicarboxylic acid therefore it must be an ortho- substituted benzaldehyde. the only ortho- substituted aromatic aldehyde having molecular formula $\bold{C_9H_{10}O}$ is 2 -ethylbenzaldehyde. all the reaction can now be explained on the basis of the structure. [figure is in the attachment]
please see the attachment given



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