The observations for the regiochemical and the stereochemical outcome for the formation of the product given have to be identified. Concept Introduction: Ring-opening of epoxide : The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction. 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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Chapter 13, Problem

Interpretation Introduction

Interpretation:

The observations for the regiochemical and the stereochemical outcome for the formation of the product given have to be identified.

Concept Introduction:

Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.

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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