when benzyl chloride is boiled with aqueous KOH solution and the solution is acidified by a few drops of dilute HNO_(3) followed by AgNO_(3) solution, a white precipitate is formed. However, no such precipitate is noticed when the reaction is carried with chlorobenzene. explain.

when benzyl chloride is boiled with aqueous KOH solution and the solut

1.	when benzyl chloride is boiled with aqueous KOH solution and the solution is acidified by a few drops of dilute HNO_(3) followed by AgNO_(3) solution, a white precipitate is formed. However, no such precipitate is noticed when the reaction is carried with chlorobenzene. explain.
Answer» Solution :In case of `C_(6)H_(5)CH_(2)Cl`, the benzyl carbocation `(C_(6)H_(5) OVERSET(o+)(C)H_(2))` FORMED by releasing `Cl^(-)` ion is resonance stabilised. THEREFORE, the `C - Cl` bond can cleave to form `KCl`. HOWEVER, the phenyl carbocation `(C_(6)overset(o+)(H)_(5))` expected to be formed in case of chlorobenzene does not show any resonance. therefore, `C - Cl` bond does not cleave in case of chlorobenzene and no white precipitate is formed in this case.