Question

An organic compound (A) with the molecular formula \[\ce{C9H10O}\] forms a 2, 4-DNP derivative, reduces Fehling solution and undergoes the Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzene dicarboxylic acid.

1. Identify the compound (A) and write its IUPAC name.  (2)
2. Write the reaction of compound (A) with
   1. 2, 4-Dinitrophenyl hydrazine and   
   2. Fehling solution.  (2)
3. Write the equation of compound (A) when it undergoes the Cannizzaro reaction.  (1)

Answer 1

1. The compound (A) is an aldehyde. The IUPAC name of the given compound is 2-ethylbenzaldehyde.
2.    
   1. 
      
   2. 
      
3. 
   
   The Cannizzaro reaction does not affect the alkyl substituent. Same products are formed.
   \[\ce{C6H4CHO(CH2CH3) + NaOH -> C6H4(CH2CH3)COO^-Na+ + C6H4(CH2CH3)CH2OH}\]