The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified. Concept Introduction: Epoxides from Peroxy acids: The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific. 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.

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Answer 1

Question

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

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Answer 2

Question

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

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Answer 3

Question

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

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Answer 4

Question

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

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Answer 5

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

Answer 6

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

Answer 7

Chapter 16.4, Problem 8ATS

Interpretation Introduction

Interpretation:

The structure of epoxides 2 and 3 and the mechanism for the formation of 4 have to be identified.

Concept Introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (mCPBA) and Peroxyacetic acid. This process is stereospecific.

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.

Answer 8

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Answer 11

Ch. 16.1 - Prob. 1CC Ch. 16.2 - Prob. 2CC Ch. 16.2 - Prob. 3CC Ch. 16.2 - Prob. 4CC Ch. 16.3 - Prob. 5CC Ch. 16.4 - Prob. 1LTS Ch. 16.4 - Prob. 6PTS Ch. 16.4 - Prob. 7PTS Ch. 16.4 - Prob. 8ATS Ch. 16.5 - Prob. 2LTS

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Chapter 16 Solutions