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Example 2: Identify all the products formed in the following reaction and indicate the major product.
Solution: Three products will be formed in the given reaction as shown below:
In this reaction the primary alcohol undergoes SN1 mechanism by forming a carbocation and then undergoing ring expansion, but primary alcohols prefer SN2 mechanism. So why is this primary alcohol undergoing SN1 mechanism?
It does not. The proposed mechanism is wrong.
The conversion of cyclopentylmethanol to 1-bromo-1-methylcyclopentane is not reported anywhere in the literature. If you could somehow generate the primary carbocation, then one would expect a rapid 1,2-hydride shift to generate the more stable tertiary carbocation, giving rise to 1-bromo-1-methylcyclopentane.
The ring-expansion product could be rationalized by a concerted 1,2-alkyl shift displacing $\ce{OH2^+}$ without violating first-principles.
