Chapter 14, Problem 42PP

(a)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(b)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(c)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(d)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(e)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(f)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(g)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.

(h)

Interpretation Introduction

Interpretation: The products for the given reactions 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.

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the less substituted position.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $\text{H}\text{\& OH}$ groups across the double bond of alkene.

Useful reagents:

1. 1. $\text{NaSH}$: A very strong nucleophile that will react with an epoxide in a ring-opening reaction.