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

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Question : 17 of 31
Marks: +1, -0
Out of C6H5CH2ClC_6H_5CH_2Cl and C6H5CHClC6H5C_6H_5CHClC_6H_5, which is more easily hydrolysed by aqueous KOH?
Solution:  
C6H5CHClC6H5C_6H_5CHClC_6H_5 is hydrolysed faster.
(a) Hydrolysis of an alkyl halide is an example of nucleophilic substitution reaction. In case of aryl halides this follows the SN1S_N1 pathway i.e., via the formation of carbocation.
(b) C6H5CH2ClC_6H_5CH_2Clor 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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