Chapter 9.16, Problem 33P

Interpretation Introduction

(a)

Interpretation: The product of given reaction is to be drawn and the stereochemistry at any stereogenic center is to be indicated.

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. The mechanism of overall reaction involves two steps.

Interpretation Introduction

(b)

Interpretation: The product of given reaction is to be drawn and the stereochemistry at any stereogenic center is to be indicated.

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. The mechanism of overall reaction involves two steps.