A synthesis of phenacetin starting from benzene has to be found Concept Introduction : Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution. Williamson ether synthesis : The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H 2 ) as a bi-product. The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S N 2 mechanism. To find: Give a synthesis of phenacetin starting from benzene Apply a retrosynthetic analysis

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Answer 1

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Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

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Answer 2

Question

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

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Answer 3

Question

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

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Answer 4

Question

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

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Check out a sample textbook solution

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Answer 5

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

Answer 6

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

Answer 7

Chapter 22, Problem 77IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 22.2 - Prob. 1LTS Ch. 22.2 - Prob. 1PTS Ch. 22.2 - Prob. 2PTS Ch. 22.2 - Prob. 3ATS Ch. 22.3 - Prob. 4CC Ch. 22.3 - Prob. 5CC Ch. 22.3 - Prob. 6CC Ch. 22.3 - Prob. 7CC Ch. 22.3 - Prob. 8CC Ch. 22.3 - Prob. 9CC

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Chapter 22 Solutions