(a) Interpretation: The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated. Concept introduction: In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

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Answer 1

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Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

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The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate) (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester. (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).

One of the following esters cannot undergo the Claisen condensation. Which one? Write structural formulas for the Claisen condensation products of the other two.

Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenol

Answer 2

Question

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

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Answer 3

Question

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

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Answer 4

Question

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

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Answer 5

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

Answer 6

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Answer 7

Chapter 21, Problem 21.45AP

Interpretation Introduction

(a)

Interpretation:

The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.

Concept introduction:

The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

Solution Summary: The author explains the effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester.

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Chapter 21 Solutions