As discussed in Are You Wondering 27-2, carbocation

Chapter 27, Problem 27

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As discussed in Are You Wondering 27-2, carbocation rearrangements occur in some substitution and elimination reactions. What elimination product would you expect in the following reaction if no rearrangement of the carbocation occurs? Experiment reveals that the main product is 2,3-dimethyl-2-pentene. Suggest a mechanism that shows how 2,3-dimethyl-2-pentene is formed. [Hint: Consider the formation and rearrangement of a carbocation.]

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