Chapter 9, Problem 9.68P

Interpretation Introduction

Interpretation: A stepwise mechanism for the given reaction is to be drawn and the stereochemistry of the product is to be explained.

Concept introduction: The strong nucleophiles that open epoxide ring are ${}^{-}\text{OH,}{}^{-}\text{OR},{}^{-}\text{CN,}{}^{-}\text{SR,}\text{HC}\equiv {\text{C}}^{-},\text{and}{\text{NH}}_3$. The reaction takes place through an ${\text{S}}_{\text{N}}\text{2}$ mechanism, and yields product with inversion of configuration.