(a) Interpretation: Whether the resonance interaction increases or decreases the acidity of an α , β -unsaturated carboxylic acid is to be stated. Concept introduction: Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

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Answer 1

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Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

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(a) Draw the three isomers of benzenedicarboxylic acid.(b) The isomers have melting points of 210 °C, 343 °C, and 427 °C. Nitration of the isomers at all possible positions was once used to determine their structures. The isomer that melts at 210 °C gives two mononitro isomers. The isomer that melts at 343 °C gives three mononitro isomers. The isomer that melts at 427 °C gives only one mononitro isomer. Show which isomer has which melting point.

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).

A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyoxygen atom.(b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

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Answer 5

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

Answer 6

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Answer 7

Chapter 22, Problem 22.76AP

Interpretation Introduction

(a)

Interpretation:

Whether the resonance interaction increases or decreases the acidity of an α,β-unsaturated carboxylic acid is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The reason as to how the pKa value is consistent with the polar effect of the double bond and the resonance effect of part (a) is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The acidity of the compound is measured by the acid dissociation constant. It is represented by the symbol Ka. It is also known as ionization constant. In practical terms, it is represented in terms of the logarithm pKa=−log(Ka). More positive the value of pKa, lower is the acidity of the compound. It depends on several other factors.

Answer 10

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Answer 13

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

Solution Summary: The author explains that the resonance interaction decreases the acidity of an alpha,beta -unsaturated carboxylic acid because the conjugate base is less stable.

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