Question

An organic compound (A) of molecular formula C₇H₆O gives brisk effervescence with Na₂CO₃ . Sodium salt of (A) on treatment with sodalime gives (B) a simplest aromatic hydrocarbon. (B) on reaction with acetyichioride in the presence of anhydrous AICI₃ gives (C) of formula C₈H₈O. (C) on treatment with conc. nitric acid and conc. sulphuric acid gives (D) of formula C₈H₇NO₃ . Identify A,B,C,D,E and explain the reactions involved.

Answer 1

1. (A) gives brisk effervescence with Na₂CO₃ solution and it must be a carboxylic acid. (A) gives brisk effervescence with NNa₂CO₃ solution and it must be a carboxylic acid. (A) is C₆H₅COOH benzoic acid. 

2. Sodium salt of benzoic acid on reaction with sodalime (decarboxylation) produces benzene as (B)

3. Benzene on treatment with acetyl chloride in the presence of anhydrous AlCl₃ gives acetophenone as (C)

4. Acetophenonc on reaction with conc. HNO₃ and cone. H₂SO₄ gives m – nitro acetophenone as (D)