(a) Interpretation: The predominant product that is obtained from the monosulfonation of m − bromotoluene is to be predicted. Concept introduction: The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

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Answer 1

Question

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

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Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct. Can be more than one answer

5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.

A. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.

Answer 2

Question

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

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Answer 3

Question

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

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Answer 4

Question

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

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Answer 5

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

Answer 6

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Answer 7

Chapter 16, Problem 16.30P

Interpretation Introduction

(a)

Interpretation:

The predominant product that is obtained from the monosulfonation of m−bromotoluene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a sulfonic acid takes place is known as aromatic sulfonation. This reaction is an aromatic substitution reaction. The substitution in sulfonation reaction is reversible.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The predominant product that is obtained from the mononitration of m−bromoiodobenzene is to be predicted.

Concept introduction:

The organic reaction of an arene in which the replacement of a hydrogen atom by a nitro group takes place is known as nitration reaction. In this reaction, an aromatic compound is treated with concentrated sulfuric acid and nitric acid to form a nitro compound.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 16 - Prob. 16.1P Ch. 16 - Prob. 16.2P Ch. 16 - Prob. 16.3P Ch. 16 - Prob. 16.4P Ch. 16 - Prob. 16.5P Ch. 16 - Prob. 16.6P Ch. 16 - Prob. 16.7P Ch. 16 - Prob. 16.8P Ch. 16 - Prob. 16.9P Ch. 16 - Prob. 16.10P

Solution Summary: The author explains that the predominant product obtained from the monosulfonation of m-bromotoluene is to be predicted.

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Chapter 16 Solutions