Using oxirane as the only source of carbon, phenylbutan − 1 − ol is to be synthesized from bromobenzene . Concept introduction: Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene , because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

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Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

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Answer 2

Question

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

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Answer 3

Question

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

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Answer 4

Question

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

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Answer 5

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

Answer 6

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

Answer 7

Chapter 19, Problem 19.5P

Interpretation Introduction

Interpretation:

Using oxirane as the only source of carbon, phenylbutan−1−ol is to be synthesized from bromobenzene.

Concept introduction:

Our only source of carbon oxirane contains two C- atoms, and the product contains 10 C- atoms, so two C-C bonds must be formed. A C-C bond-forming reaction would be difficult to carry out directly between oxirane and bromobenzene, because such a reaction would entail the formation of a bond between two carbon atoms bearing a partial positive charge. The precursor should bear a carbon atom with negative or partial negative charge. One way to form a bond between two carbons of like charge is to carry out a separate reaction that first reverses the charge (or polarity) at one of the carbons. Thus, one carbon atom would become electron rich while the other would remain electron poor. This general idea of reversing a charge at a particular atom, called umpolung (a German term meaning “polarity reversal”), is a common practice in organic synthesis.

Answer 8

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Answer 11

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

Solution Summary: The author explains that oxirane is the only source of carbon, and that a bond-forming reaction between two carbon atoms would be difficult.

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