(a) An organic compound (A) of molecular formula `C_(6)H_(6)O` gives white preclpitate with bromine water. (A) on reaction with NaOH gives (B). (B) reacts with methyl lodlde in presence of dry ether gives (C) of molecular formula `C_(7)H_(8)O` which will not liberate `H_(2)` gas with metallic Na (C) reaction with acetyl chloride gives (D) and (E) of formula which are position isomers. Identify A,B,C,D &E and explain the reaction
(b ) (i) What happens when n-propyl benzene is oxidised using `H^(+)//KMnO_(4)`
(ii) Identify A,B, andC

Explanation

a 1. An organic compound gives white precipitate with bromic water means it must be a phenol from the molecular formula it is identified as `C_(6)H_(5)OH`
2. Phenol on reaction with NaOH gives (b) as sodium phenoxide `C_(6)H_(5) ONa`

3. Sodium phenxide on reaction with methyl iodide in the pressure of dry ether undergo Williamsons synthesis and gives Anisole as (C )

4. Anisole on reaction with acetly chloride undergoes Friedel Craft acetylation yield o-methoxy acetophenone and p- methoxy acetphenone as (d ) and (E )