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Haloalkanes And Haloarenes

Question
CBSEENCH12007612

In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?

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Solution

Greater the stability of the carbocation, faster is the rate of SN1 reaction. Since tertiary carbocation 2-chloro-2-methylpropane is more stable than secondary carbocation 3-chloropentane. Hence SN1 reaction proceed via tertiary cation such as 2-chloro-2-methylpropane.