In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed. Concept introduction: An aromatic compound is more stable than nonaromatic and antiaromatic compounds. Resonance is the delocalization of the electrons within a molecule. Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond. Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

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Answer 1

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Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

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Answer 2

Question

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

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Answer 3

Question

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

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Answer 4

Question

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

Expert Solution & Answer

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Answer 5

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

Answer 6

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

Answer 7

Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles, while one on C1 is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.

Answer 8

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Answer 11

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Solution Summary: The author explains the nucleophilic aromatic substitution reaction based on the addition–elimination mechanism.

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