
Concept explainers
(a)
Interpretation:
The mechanism for the given conversion has to be identified and the stereochemical outcome has to be justified.
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.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions
(b)
Interpretation:
The product of the given process has to be predicted.
Concept introduction:
Sharpless epoxidation: An
Sharpless catalyst consists of Titanium tetraiospropoxide and one enantiomer of Diethyl tartrate (
A chiral complex is formed with Titanium tetraisopropoxide and with either

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Chapter 13 Solutions
Organic Chemistry, Third Edition Binder Ready Version
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