Q2 of 47 Page 1

Why is CH2=CH-CH2-Cl more easily hydrolysed than CH3CH2CH2Cl?

CH2=CH-CH2-Cl more easily hydrolysed than CH3CH2CH2Cl because on hydrolysis of CH2=CH-CH2-Cl, allyl carbocation is formed i.e. CH2=CH-CH2+ which is resonance stabilized whereas on hydrolysis of CH3CH2CH2Cl, propyl carbocation i.e. CH3CH2CH2+ which is only stabilized by inductive effect. Carbocation is more stabilized by resonance effect thus CH2=CH-CH2-Cl is more easily hydrolysed.


CH2=CH-CH2+ +CH2-CH=CH2


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