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a solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl which one of these is easily hydrolysed and why?

Question

a solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl which one of these is easily hydrolysed and why?

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Solution

The compound CH3CHClCH2CH3 is more easily hydrolysed than CH3CH2CH2CH2Cl. This is because CH3CHClCH2CH3 is a secondary alkyl halide, while CH3CH2CH2CH2Cl is a primary alkyl halide.

In an aqueous solution of KOH, hydrolysis occurs through a nucleophilic substitution reaction. Secondary alkyl halides are more reactive towards nucleophilic substitution than primary alkyl halides because the partial positive charge on the carbon atom (which is attached to the halogen) in secondary alkyl halides is more effectively stabilized by the neighboring alkyl groups through inductive effect and hyperconjugation.

Therefore, CH3CHClCH2CH3 is more easily hydrolysed than CH3CH2CH2CH2Cl.

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