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Question
Out of 
, which is more reactive towards SN1 reaction and why?
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Solution
Since formation of carbocation is the rate-determining step in the SN1 reaction, the stability of carbocation would determine its reactivity.
The order of stability of carbocation is as follows:
Tertiary > Secondary > Primary >Methyl
Here, 1-chloro-1-methylpropane would form secondary carbocation, while 1-chloro-2-methylpropane will form primary carbocation, which is less stable than secondary carbocation. Hence, reactivity towards the SN1 reaction would be higher for 1-chloro-1-methylpropane.
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