The relative amount of trans-tetrol to cis-tetrol at pH 12 larger than at pH 3; the reason has to be discussed. Concept Introduction: Epoxides : are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved. Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide. Acid-catalyzed hydrolysis of an epoxide via S N 2 process:

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Answer 1

Question

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

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Answer 2

Question

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

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Answer 3

Question

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

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Answer 4

Question

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

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Answer 5

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

Answer 6

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

Answer 7

Chapter 11.9, Problem DQ

Interpretation Introduction

Interpretation:

The relative amount of trans-tetrol to cis-tetrol at pH12 larger than at pH 3; the reason has to be discussed.

Concept Introduction:

Epoxides: are more reactive than simple ethers due to three membered ring strains. Reaction of epoxides with nucleophiles opens the ring by which the ring strain is relieved.

Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.

Acid-catalyzed hydrolysis of an epoxide via SN2 process:

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 11.2 - Write IUPAC and common names for these ethers. (a)...Ch. 11.3 - Arrange these compounds in order of increasing...Ch. 11.4 - Show how you might use the Williamson ether...Ch. 11.4 - Show how ethyl hexyl ether might be prepared by a...Ch. 11.5 - Account for the fact that treatment of tert-butyl...Ch. 11.5 - Draw structural formulas for the major products of...Ch. 11.6 - Prob. 11.7P Ch. 11.8 - Draw the expected products of Sharpless...Ch. 11.9 - Prob. AQ Ch. 11.9 - Prob. BQ

Solution Summary: The author explains that epoxides are more reactive than simple ethers due to three membered ring strains. Ring opening takes place by acid-catalyzed hydrolysis.

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Chapter 11 Solutions