The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group. Concept introduction: Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C − O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Question

Want to see the full answer?

Answer 1

Question

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw a complete, detailed mechanism for this reaction.

Please predict the product of the following reaction, and draw the complete, detailed mechanism.

Draw the complete, detailed mechanism for the reaction shown here. Will the product be optically active? Explain.

Answer 2

Question

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Answer 6

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Answer 7

Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains that nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept explainers

Videos

Want to see the full answer?

Chapter 10 Solutions