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Question 38

The major product in the following reaction is:

  • Step 1: Protonation and Formation of the Carbocation

    The starting material is a cyclopentane ring with a tertiary alcohol substituent group (specifically containing two methyl groups at the alpha position, as derived from the structures). Protonation of the hydroxyl group ($$\text{-OH}$$) by the acid turns it into an excellent leaving group ($$\text{-OH}_2^+$$). Water is eliminated, leaving behind a secondary carbocation outside the ring.

  • Step 2: Wagner-Meerwein Ring Expansion

    The initial carbocation is adjacent to a strained five-membered cyclopentane ring. To relieve angle strain and form a more stable ring, a 1,2-alkyl shift occurs where one of the C-C bonds of the cyclopentane ring breaks and migrates to the carbocation carbon. This expands the five-membered ring into a much more stable six-membered cyclohexyl carbocation ring system.

  • Step 3: Deprotonation to Form the Most Stable Alkene

    Finally, a water molecule acts as a weak base and removes a proton ($$\text{H}^+$$) from the adjacent carbon atom to establish a double bond. Following Zaitsev's Rule, elimination happens to yield the most highly substituted, conjugated, and thermodynamically stable tetrasubstituted alkene possible.


Conclusion:

The ring expansion transforms the cyclopentane framework into a cyclohexane ring containing a double bond between two carbons that both bear a methyl group. This corresponds to 1,2-dimethylcyclohexene, which is illustrated as the correct option in Option B.

Answer: Option B

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