A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol . Concept Introduction: Primary alcohols form ethers when they are heated in the presence of an acid catalyst. Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water. In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion. In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion. In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

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Answer 1

Question

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

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Answer 2

Question

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

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Answer 3

Question

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

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Answer 4

Question

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

Expert Solution & Answer

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Answer 5

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

Answer 6

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

Answer 7

Chapter 16.7, Problem 7P

Interpretation Introduction

Interpretation:

A stepwise mechanism is to be written for the acid catalyzed formation of oxane from 1,5-pentanediol.

Concept Introduction:

Primary alcohols form ethers when they are heated in the presence of an acid catalyst.

Two molecules of the alcohol undergo condensation and form a larger molecule, that is ether and a smaller molecule, which is water.

In the first step, the alcohol is protonated by the acid catalyst producing an alkoxonium ion.

In the second step, another alcohol molecule acts as a nucleophile and attacks the alkoxonium ion.

In the final step, the de-protonation of alkoxonium ion takes place to form the ether molecule.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 16.2 - Prob. 1P Ch. 16.2 - Prob. 2P Ch. 16.4 - Prob. 3P Ch. 16.5 - Prob. 4P Ch. 16.5 - Give the structures, including stereochemistry,...Ch. 16.5 - Prob. 6P Ch. 16.7 - Prob. 7P Ch. 16.8 - Prob. 8P Ch. 16.8 - Prob. 9P Ch. 16.9 - Predict the principal organic product of each of...

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