Question
An organic compound with the molecular formula $C _9 H _{10} O$ forms 2,4-DNP derivative, reduces Tollens' reagent and undergoes Cannizzaro reaction. On vigorous oxidation it gives 1,2-benzene dicarboxylic acid. Identify the compound.
✓
Answer
This organic compound forms 2,4-DNP derivative. So this will be carbonyl compound (Aldehyde or Ketone).
But it reduces Tollens' reagent so this is Aldehyde and giving Cannizzaro reaction, hence $\alpha- H$ are absent in it. Oxidation of it forms 1,2-benzene dicarboxylic acid.
Oxidation product proves that it have one benzene ring, one - COOH group forms from oxidation of - CHO group and another - COOH group by the oxidation of Alkyl group. So according to molecular formula the structural formula of this will be :
But it reduces Tollens' reagent so this is Aldehyde and giving Cannizzaro reaction, hence $\alpha- H$ are absent in it. Oxidation of it forms 1,2-benzene dicarboxylic acid.
Oxidation product proves that it have one benzene ring, one - COOH group forms from oxidation of - CHO group and another - COOH group by the oxidation of Alkyl group. So according to molecular formula the structural formula of this will be :
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