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When a primary carbocation is formed adjacent to a highly strained cyclobutane ring (e.g., cyclobutyReaction Mechanism Chemistry Question

Question

When a primary carbocation is formed adjacent to a highly strained cyclobutane ring (e.g., cyclobutylmethyl cation), it rapidly undergoes a structural change to maximize stability. What is this process called?

Answer: C

💡 Solution & Explanation

A primary carbocation adjacent to a strained 4-membered ring is highly unstable. It relieves significant angle and torsional strain by undergoing an alkyl shift where one of the ring carbon-carbon bonds breaks and reattaches to the carbocation center. This expands the ring to a 5-membered ring containing a more stable secondary carbocation.

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