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A solution of aqueous of KO hydrolysis C...

A solution of aqueous of KO hydrolysis `CH_(3)CHClCH_(2)CH_(3) and CH_(3)CH_(2)CH_(2)CH_(2)Cl`. Which one of these is more easily hydrolysed.?

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Under aqueous conditions, substitution occurs by `S_(N)1` mechanism since carbocation intermediates are stabilized by solvation. Further, the reactivity in `S_(N)1` reactions depends upon the stability of carbocations.
`CH_(3)-CHCl-CH_(2)CH_(3) overset("Ionization")to underset(2^(@)" carbocation (more stable)")(CH_(3)-overset(+)(C)H-CH_(2)CH_(3)+Cl^(-))`
`CH_(3)CH_(2)CH_(2)CH_(2)-Cl overset("Ionization")to underset(1^(@)" carbocation (less stable)")(CH_(3)CH_(2)CH_(2)overset(+)(C)H_(2)+Cl^(-))`
Now since `CH_(3)CHClCH_(2)CH_(3)` upon ionization gives the more stable `2^(@)` carbocation while `CH_(3)CH_(2)CH_(2)CH_(2)Cl` on ionization gives the less stable `1^(@)` carbocation, therefore, `CH_(3)CHClCH_(2)CH_(3)` hydrolyses faster than `CH_(3)CH_(2)CH_(2)CH_(2)Cl`.
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