A complete, detailed mechanism is to be drawn for the given reaction. Concept introduction: One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction. This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH − , which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

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Answer 1

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Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

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Answer 2

Question

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

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Answer 3

Question

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

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Answer 4

Question

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

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Answer 5

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

Answer 6

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

Answer 7

Chapter 8, Problem 8.59P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

One way to synthesize diethyl ether is to heat ethanol in the presence of a strong acid. This is an example of a nucleophilic substitution reaction. In the first step of the mechanism, the strong acid will protonate the OH group in ethanol. This is a proton transfer reaction.

This step is necessary. If nucleophilic substitution were to take place first instead, the leaving group would come off as OH−, which is a strong base and is not compatible with the acidic conditions. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that interfere with the reaction medium.

Answer 8

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Answer 10

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Answer 11

Ch. 8 - Prob. 8.1P Ch. 8 - Prob. 8.2P Ch. 8 - Prob. 8.3P Ch. 8 - Prob. 8.4P Ch. 8 - Prob. 8.5P Ch. 8 - Prob. 8.6P Ch. 8 - Prob. 8.7P Ch. 8 - Prob. 8.8P Ch. 8 - Prob. 8.9P Ch. 8 - Prob. 8.10P

Solution Summary: The author explains that a proton transfer reaction is handy and can be used to avoid non-compatible species that interfere with the reaction medium.

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