Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following reaction sequence.
Correct answer
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Step-by-step solution
The reaction sequence involves a Payne rearrangement followed by an epoxide ring opening. 1. Payne Rearrangement: The starting material is an epoxy alcohol. In the presence of a base ( NaOH ), the primary hydroxyl group is deprotonated to form an alkoxide. This alkoxide undergoes an intramolecular S _ N 2 attack on the adjacent epoxide carbon (C2), opening the original internal epoxide and forming a new, more reactive terminal epoxide. Because this is an S _ N 2 process, the stereocenter at C2 undergoes inversion o