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The Cannizaro Reaction

An organic co...

Question

An organic compound with the molecular formula $C_{9} H_{10} O$ forms 2, 4 - DNP derivative, reduces Tollen's reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2 - benzene diearboxylic acid. Identify the compound.

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Solution

(i) The compound with molecular formula $C_{9} H_{10} O$ forms a 2, 4 - DNP derivative and reduces Tollen's reagent, so it is an aldehyde.

(ii) It undergoes Connizzaro reaction, so the aldehyde group should be directly attached to the benzene ring.

(iii) On vigorous oxidation, it gives 1, 2 - benzene dicarboxylic acid, so it should be an ortho-substituted benzaldehyde. For molecular formula $C_{9} H_{10} O$ , the possibility is only o - ethyl benzaldehyde.

(iv) The equations for all the reactions are given below :

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The Cannizaro Reaction

Standard XII Chemistry

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