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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4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO

b. H3C CH3 H3O+ ✓ H OH

2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3

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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