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Question

Out of CH3CHCH2Cl|CH3 and CH3CH2CHCl|CH3,
which is more reactive towards SN1 reaction and why?

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Solution

Since the first step of the SN1 reaction is loss of a leaving group to give a carbocation, the reactivity will be proportional to the stability of the carbocation. Carbocation stability increases with increasing substitution of the carbon (tertiary > secondary > primary).

CH3CH(CH3)CH2Cl (1-chloro-2-methyl propane) forms carbocation CH3CH(CH3)CH+2

CH3CH2CH(CH3)Cl (2-chlorobutane ) forms carbocation CH3CH2(CH3)CH+
which is more stable and thus the compound 2chlorobutane is more reactive than 1chloro2methylpropane isomer.

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