Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product of the following pinacol rearrangement reaction:
Correct answer
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Step-by-step solution
The given reaction is a pinacol rearrangement of a symmetrical diol, 2,2'-bi(bicyclo[2.2.1]heptan-2-yl)-2,2'-diol. Protonation of one of the hydroxyl groups by concentrated H₂SO₄ followed by the loss of a water molecule generates a carbocation at the C2 position of one of the norbornane rings. To stabilize this carbocation, a 1,2-alkyl shift occurs from the adjacent C2' carbon of the second norbornane ring. The two possible migrating groups on C2' are the C1' bridgehead carbon and the C3' methylene carbon. Migratio