Chapter 9, Problem 59P

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.

Interpretation Introduction

(e)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.

Interpretation Introduction

(f)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile $\left({\text{:Nu}}^{-}\right)$ or an acid $\left(\text{HZ}\right)$. The mechanism of the reaction with ${\text{:Nu}}^{-}$ is ${\text{S}}_{\text{N}}\text{2}$, and the mechanism of the reaction with $\text{HZ}$ is in between ${\text{S}}_{\text{N}}\text{2}\text{and}{\text{S}}_{\text{N}}1$.