?Alcohol functions can be protected as tetrahydropyranyl ethers (THPs) by acid-catalyzed

Chapter 18, Problem 18.45

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Alcohol functions can be protected as tetrahydropyranyl ethers (THPs) by acid-catalyzed addition to dihydropyran according to the equation:

Addition of the alcohol to dihydropyran is regiospecific in that I is formed to the exclusion of II. Suggest a mechanistic reason for the observed regioselectivity.

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