Question

Out of C₆H₅CH₂Cl and C₆H₅CHClC₆H₅, which is more easily hydrolysed by aqueous KOH.

Answer 1

C₆H₅CHClC₆H₅ is hydrolysed faster.

1. The hydrolysis of an alkyl halide is a nucleophilic substitution reaction. For aryl halides, this occurs through the S_N1 method, resulting in carbocation.
2. C₆H₅CH₂Cl or benzyl chloride gives carbocation while C₆H₅CHClC₆H₅ generates .
3. Out of I and II, carbocation II is more stable. Two attached phenyl rings on the carbon carry the positive charge.
4. This leads to increased delocalisation of the positive charge and greater carbocation stability. This leads to faster formation of (II) and easier hydrolysis of the resulting halide than benzyl chloride.