Chapter 14, Problem 50PP

Interpretation Introduction

Interpretation: The products for the following reaction scheme to be predicted.

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.

Alkoxymercuration-demercuration: The process converts an alkene into alcohols, which results in the markovnikov’s addition of $\text{H \& OH}$ groups across the double bond of alkene.