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Aldehydes, Ketones and Carboxylic Acids
Question
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An organic compound with the molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound. 

Answer

The given molecular formula C9H10O 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 above mechanism is given as,

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Some More Questions From Aldehydes, Ketones and Carboxylic Acids Chapter

Write the structures of the following reactions:

Write the structures of products of the following reactions:


    

Arrange the following compounds in increasing order of their boiling points:
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3.

Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions:    
Ethanal, Propanal, Propanone, Butanone.

Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions:    
Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.

Predict the products of the following reactions:

Predict the products of the following reactions:

Predict the products of the following reactions: