An organic compound with the molecular formula C8H8O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzene dicarboxylic acid. The organic compound is

Question

An organic compound with the molecular formula C8H8O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzene dicarboxylic acid. The organic compound is (A) 2-ethylbenzaldehyde (B) 2-methylbenzaldehyde (C) acetophenone (D) 3-methylbenzaldehyde

Tardigrade Admin · Accepted Answer

Since, the compound forms 2,4 -DNP derivative, so it must be a carbonyl compound. It reduces tollen's Reagent and undergoes Cannizzaro reaction, so it must contain a - CHO group and no α - H atoms. Thus, its possible formula may be CH 3 C 6 H 4 CHO. Since, it gives 1, 2-benzene-dicarboxylic acid when subjected to oxidatin, so - CH 3 and - CHO groups must be present at successive positions. Thus, the structure of the compound must be

The reactions occurring are as follows

Q. An organic compound with the molecular formula $C_{8} H_{8} O$ forms $2, 4 - D NP$ derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives $1, 2$ -benzene dicarboxylic acid. The organic compound is

2-ethylbenzaldehyde

2-methylbenzaldehyde

acetophenone

3-methylbenzaldehyde

phenylacetaldehyde