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Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH? - Chemistry

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Question

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

Solution

Hydrolysis by aqueous KOH proceeds through the formation of carbocation. If carbocation is stable, then the compound is easily hydrolyzed by aqueous KOH. Now,  `C_6H_5CH_2Cl` forms 1°-carbocation, while C6H5CHClC6H5 forms 2°-carbocation, which is more stable than 1°-carbocation. Hence,  `C_6H_5CHClC_6H_5` is hydrolyzed more easily than `C_6H_5CH_2Cl` by aqueous KOH.

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APPEARS IN

 NCERT Solution for Chemistry Textbook for Class 12 (2018 (Latest))
Chapter 10: Haloalkanes and Haloarenes
Q: 17 | Page no. 312
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Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH? Concept: Chemical Reactions of Haloalkanes and Haloarenes - Reactions of Haloalkanes - Nucleophilic Substitution Reactions.
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