An SN1 reaction occurs through the formation of a carbocation intermediate. Alkyl halide (I) is tertiary (3°), whereas (II) is secondary (2°). As a result, (I) forms a tertiary carbocation, while (II) forms a secondary carbocation. Since the rate of an SN1 reaction increases with carbocation stability, and a tertiary carbocation is more stable than a secondary carbocation, compound (I), i.e., 2-chloro-2-methylpropane, undergoes the SN1 reaction faster than compound (II), i.e., 3-chloropentane.
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Questions
In the following pair of halogen compounds, which compound undergoes a faster SN1 reaction?
In the following pair of halogen compounds, which compound undergoes SN1 reaction faster and why?
Short Answer
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Solution 1
The activity of halogen compounds in SN1 reaction depends on the stability of the carbocation formed due to ionization. The order of stability is tertiary > secondary > primary. Hence, 3° alkyl chloride is more active than 2° alkyl chloride. Hence, 2° alkyl chloride is more active in SN1 reaction.
will react faster. The carbocation 
will be more stable and hence the reaction will be faster.
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Solution 2
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Notes
Students should refer to the answer according to their questions.
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Chapter 6: Haloalkanes and Haloarenes - Intext Question [Page 186]
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