A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable. Concept introduction: An S N 1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product. The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Question

Want to see the full answer?

Answer 1

Question

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

The reaction shown here proceeds via a carbocation rearrangement. Draw a complete, detailed mechanism to account for the product. Explain why the carbocation rearrangement is favorable. CH;OH Br

Draw the complete, detailed mechanism (curved arrows) for the following reaction. Br 2. H₂O OK

Draw the product and mechanism for the reaction below. Include all major resonance structures.

Answer 2

Question

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Answer 6

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

Answer 7

Chapter 8, Problem 8.58P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn that accounts for the given product. It is also to be explained why the carbocation rearrangement is favorable.

Concept introduction:

An SN1 reaction is a two-step reaction. In the first step, the leaving group breaks off, taking its bond pair with the carbon atom, thus forming a carbocation. In the second step, the incoming nucleophile attacks the carbocation, forming the product.

The carbocation formed in the first step can rearrange to another one as a result of resonance (delocalization) if it is adjacent to a double or triple bond. A 1, 2-hydride shift or a 1, 2-methyl shift is also a possibility if it leads to the formation of a more stable carbocation. A rearrangement like this can lead to the formation of two constitutional isomers. The difference in the carbon skeleton points out that the rearrangement could have taken place. The more stable carbocation is favored over the ones that are not stable.

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. 8 - Prob. 8.1P Ch. 8 - Prob. 8.2P Ch. 8 - Prob. 8.3P Ch. 8 - Prob. 8.4P Ch. 8 - Prob. 8.5P Ch. 8 - Prob. 8.6P Ch. 8 - Prob. 8.7P Ch. 8 - Prob. 8.8P Ch. 8 - Prob. 8.9P Ch. 8 - Prob. 8.10P

Solution Summary: The author explains that the carbocation rearrangement in the first step is favorable as it is resonance stabilized.

Concept explainers

Videos

Want to see the full answer?

Chapter 8 Solutions