NCERT Class XII Chemistry
Chapter - Haloalkanes and Haloarenes
Questions with Solutions

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Question : 17
Total: 31
Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH?
Solution:  
C6H5CHClC6H5 is hydrolysed faster.
(a) Hydrolysis of an alkyl halide is an example of nucleophilic substitution reaction. In case of aryl halides this follows the SN1 pathway i.e., via the formation of carbocation.
(b) C6H5CH2Clor benzyl chloride gives
(c) Out of I & II, carbocation II is more stable. The reason is the presence of two phenyl rings attached to the carbon carrying the positive charge.
(d) As a result, the delocalisation of the +ve charge is greater and the carbocation is more stable. Due to this, (II) is formed faster and the corresponding halide is hydrolysed with greater ease as compared to benzyl chloride.
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