The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified. Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed. Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

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Answer 1

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 2

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 3

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 4

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 5

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 6

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

Answer 7

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 9

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 13.2 - Prob. 1LTS Ch. 13.2 - Prob. 1PTS Ch. 13.2 - Prob. 2PTS Ch. 13.2 - Prob. 3ATS Ch. 13.4 - Prob. 4CC Ch. 13.5 - Prob. 2LTS Ch. 13.5 - Prob. 5PTS Ch. 13.5 - Prob. 6ATS Ch. 13.5 - Prob. 7CC Ch. 13.5 - Prob. 8CC

Solution Summary: The author explains the reagents used for synthesis of epoxide 2 to allylic alcohol 1 and the mechanism for the preparation of orthoester 4.

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