Monday, June 17, 2019

organic chemistry - Hydrolysis of 3,4-dihydropyran


In the 3,4-dihydropyran shown below will the oxygen or the pi electrons of the double bond attack the hydrogen cation during hydrolysis and why?


This is my attempt towards a solution: The oxygen lone pair clearly can attack the hydrogen cation better than the pi electrons being a better a nucleophile, but according to my textbook (T.W.Grahams Solomons) the pi electrons of the double bond attacks, but shouldn't the oxygen atom be a better nucleophile than the pi electrons?


3,4-dihydropyran




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