Question

An organic compound (A) of molecular formula C₆H₅CI on reaction with aqueous NaOH gives (B) of formula C₆H₆O. (B) on reaction with NaOH gives (C) of formula C₆H₅ONa. (C) on treatment with CO₂ , followed by acid hydrolysis yield (D) of formula C₇H₆O₃ an aromatic hydroxy acid. Identify A, B, C, D and explain the reactions involved.

Answer 1

1. (A) is identified from the formula as C₆H₅CI – Chloro benzene. 

2. Chloro benzene on treatment with aqueous NaOH yeilds C₆H₅OH – phenol as (B). 

3. Phenol on reaction with NaOH produces sodium phenoxide C₆H₅ONa as (C). 

4. Sodium phenoxide on reaction with CO₂ , followed acid hydrolysis, Kolbe’s reaction takes place to give Salicylic acid as (D).