The mechanism for the given reaction is to be proposed. Concept introduction: Benzene undergoes electrophilic- aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl 3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

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Answer 1

Question

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

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Answer 2

Question

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

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Answer 3

Question

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

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Answer 4

Question

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

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Answer 5

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

Answer 6

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

Answer 7

Chapter 22, Problem 22.51P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

Benzene undergoes electrophilic-aromatic substitution reactions in which the hydrogen atom in the aromatic system is replaced by an electrophile. Carbon atoms in epoxides are not electrophilic, but they can be made electrophilic if the catalyst AlCl3 is used. Note that the reaction does not take place without the presence of aluminum chloride. The oxygen atom attacks the electropositive aluminum in aluminum chloride to form a complex. This generates carbon electrophile. Thus, the epoxide ring can be opened by weak nucleophiles like benzene. Aluminum chloride is regenerated, so it is a catalyst. The proton transfer reaction regenerates the aromatic ring, and alcohol is formed as the major product.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

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Chapter 22 Solutions