Out of `C_(6)H_(5)CH_(2)CL`and `C_(6)H_(5)CHCIC_(6)H_(5)`, which is more easily hydrolysed by aqueous KOH?

Explanation

In aqueous solution, hydrolysis of phenyl subsituted methyl halides will occur preferably by `S_(N)1` pathway. Thus the reactivity of the given compounds will be determined by the stability of the corresponding carbocations. As `(C_(6)H_(5))_(2)overset(o+)(C)H` is more stable than `C_(6)H_(5)overset(o+)(C)H_(2), C_(6)H_(5)CHClC_(6)H_(5)` undergoes hydrolysis at a much faster rate than `C_(6)H_(5)CH_(2)Cl`.

More stable carbocation (greater no. of resonance structure)

Less stable carbocation (lesser no. of resonance structure).