Concept explainers
Interpretation:
The mechanism for the given reaction has to be proposed.
Concept Introduction:
Ring-opening of
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: When the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions.
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Essential Organic Chemistry (3rd Edition)
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning