Dehydration of alcohols proceeds via carbocation intermediates (and rearrangements if needed), giving the more stable alkene as the major product. Which of the following represents product P1 in a dehydration reaction of an appropriate alcohol via carbocation mechanism (assuming a rearrang

Question

Dehydration of alcohols proceeds via carbocation intermediates (and rearrangements if needed), giving the more stable alkene as the major product. Which of the following represents product P1 in a dehydration reaction of an appropriate alcohol via carbocation mechanism (assuming a rearrangement gives a more stable ring intermediate)?

Accepted Answer

1-Methylcyclohexene. The question refers to dehydration of an alcohol that, after initial carbocation formation at a secondary carbon attached to a cyclopentane ring, undergoes a 1,2-hydride or alkyl shift to give a more stable tertiary carbocation via ring expansion to a cyclohexyl system. The tertiary carbocation on the cyclohexane ring then loses a proton to give the more substituted alkene: 1-methylcyclohexene (trisubstituted, most stable). This is the major product P1.

Solution

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