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.

Question

Want to see the full answer?

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ

2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Want to see the full answer?

Chapter 13 Solutions