An organic compound (A) of molecular formula C_6H_6Ogives white precipitate with bromine water. (A) on reaction with NaOH gives (B). (B) reacts with methyl iodide in presence of dry ether gives (C) of molecular formula C_7H_8O which will not liberate H2 gas with metallic Na. (C) on reaction with acetyl chloride gives (D) and (E) of formula which are position isomers. Identify A, B, C, D & E and explain the reaction.

An organic compound (A) of molecular formula C_6H_6Ogives white precip

1.	An organic compound (A) of molecular formula C_6H_6Ogives white precipitate with bromine water. (A) on reaction with NaOH gives (B). (B) reacts with methyl iodide in presence of dry ether gives (C) of molecular formula C_7H_8O which will not liberate H2 gas with metallic Na. (C) on reaction with acetyl chloride gives (D) and (E) of formula which are position isomers. Identify A, B, C, D & E and explain the reaction.
Answer» Solution :(i) An organic compound gives WHITE precipitate with bromine water MEANS it must be a PHENOL. From the molecular formula it is identified as `C_6H_5OH`. (ii) Phenol on reaction with NaOH gives (B) as sodium phenox `C_6H_5ONa`. (i) Sodium phenoxide on reaction with methyl iodide in the pressure of dry ether undergo Williamsons synthesis and gives Anisole as (C). (iv) Anisole on reaction with acetyl CHLORIDE undergoes Friedel Craft.s ACETYLATION and vicid o-methoxy acetophenone and p-methoxy acetophenone as (D) and (E).