(a) Interpretation: The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated. Concept introduction: Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Question

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Answer 1

Question

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

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Answer 2

Question

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

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Answer 3

Question

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

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Answer 4

Question

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

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Answer 5

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

Answer 6

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Answer 7

Chapter 22, Problem 22.1P

Interpretation Introduction

(a)

Interpretation:

The structure of diethyl malonate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen that carries positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Answer 8

Expert Solution

Answer to Problem 22.1P

The structure of the diethyl malonate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 1

The diethyl malonate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

In diethyl malonate the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 3

Figure 1

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl group increases the polar effect and stabilize the enolate ion. The diethyl malonate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

The acidity of the carbonyl compound is directly proportional to the stability of the enolate ion. The conjugate base stabilized by delocalization of diethyl malonate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 4

Figure 2

Answer 13

Conclusion

The structure of the diethyl malonate showing acidic hydrogens is given in Figure 2. The diethyl malonate is more acidic than ordinary ester due to delocalization of negative charge in its conjugate base.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.

Conclusion

The structure of ethyl acetoacetate is shown in Figure 3 and the acidic character of ethyl acetoacetate is shown in Figure 4.

Answer 15

Interpretation Introduction

(b)

Interpretation:

The structure of ethyl acetoacetate showing acidic hydrogens is to be stated. The reason as to why it is more acidic than ordinary ester is to be stated.

Concept introduction:

Acidic hydrogen is defined as hydrogen carry positive charge when the acid dissociates. The acidity in esters depends upon the stability of enolate ion. The higher is the stability of enolate ion higher is the acidity.

Answer 16

Expert Solution

Answer to Problem 22.1P

The structure of ethyl acetoacetate showing acidic hydrogens is given below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 5

The ethyl acetoacetate is more acidic than ordinary ester because its conjugate base is stabilized by delocalization of negative charge as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

In ethyl acetoacetate, the methylene group is surrounded by two carbonyl groups as shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 7

Figure 3

This active hydrogen is abstracted by base and generates a negative charge. The negative charge is delocalized between carbon and oxygen. This delocalization stabilizes the enolate ion. However, the presence of two carbonyl groups increases the polar effect and stabilize the enolate ions. The conjugate base stabilized by delocalization of ethyl acetoacetate is shown below.

Organic Chemistry, Chapter 22, Problem 22.1P , additional homework tip 8

Figure 4

The ethyl acetoacetate is more acidic than ordinary ester as its conjugate base is stabilized by delocalization of negative charge.