The conditions used for nitration and the form of aniline present under those conditions. Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated. Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 ο C . The major product is meta isomer because nitro group is electron with-drawing substituent.

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Answer 1

Question

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

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1 Please provide an efficient synthesis of the product below from the starting material. Use the starting material as the ONLY source of carbon atoms. Show the synthesis of each compound that would be used in the overall synthesis of the product. [This synthesis uses alkyne and alcohol chemistry.]

Answer 2

Question

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

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Answer 3

Question

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

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Answer 4

Question

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

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Answer 5

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 6

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 7

Chapter 17.7, Problem 17.10P

(a)

Interpretation Introduction

To determine: The conditions used for nitration and the form of aniline present under those conditions.

Interpretation: The conditions used for nitration and the form of aniline present under those conditions are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 8

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 9

(b)

Interpretation Introduction

To determine: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product.

Interpretation: The reason for nitration of aniline being sluggish and formation of meta substituted isomer as major product are to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 10

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 11

(c)

Interpretation Introduction

To determine: The reason for formation of major para substituted product during nitration of acetanilide.

Interpretation: The reason for formation of major para substituted product during nitration of acetanilide is to be stated.

Concept introduction: The reactivity of nitrobenzene toward electrophilic aromatic substitution is less than benzene. More concentrated sulfuric and nitric acid is required for nitration of nitrobenzene. The temperature is also above 100 οC. The major product is meta isomer because nitro group is electron with-drawing substituent.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 17.1 - Prob. 17.1P Ch. 17.2 - Prob. 17.2P Ch. 17.3 - Prob. 17.3P Ch. 17.4 - Use resonance forms to show that the dipolar sigma...Ch. 17.6A - Prob. 17.5P Ch. 17.6A - Prob. 17.6P Ch. 17.6B - Propose a mechanism for the brommation of...Ch. 17.6B - Prob. 17.8P Ch. 17.6B - Prob. 17.9P Ch. 17.7 - Prob. 17.10P

Solution Summary: The author analyzes the reactivity of nitrobenzene toward electrophilic aromatic substitution and the formation of meta substituted isomer as major product.

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Chapter 17 Solutions