Based on charge stability, it is be determined why the protonation of the oxygen in the C=O group takes place selectively when there is another oxygen atom that can be protonated. Concept introduction: For a proton transfer reaction, the stability of a particular species depends on the following factors in the given order: charge, atom, resonance delocalization, and inductive effects. If protonation occurs at the same atom, then resonance delocalization effects needs to be considered. Stability of a particular structure increases as the number of atoms over which a charge is shared increases. A positive charge on a less electronegative atom is more stable than a positive charge on a more electronegative atom. In the acid catalyzed reaction of an ester, the first step in the mechanism is believed to be the protonation of the oxygen atom in the C=O group. The acid catalyzed hydrolysis of an ester converts an ester into a carboxylic acid .

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Answer 1

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 6, Problem 6.65P

Interpretation Introduction

Interpretation:

Based on charge stability, it is be determined why the protonation of the oxygen in the C=O group takes place selectively when there is another oxygen atom that can be protonated.

Concept introduction:

For a proton transfer reaction, the stability of a particular species depends on the following factors in the given order: charge, atom, resonance delocalization, and inductive effects. If protonation occurs at the same atom, then resonance delocalization effects needs to be considered. Stability of a particular structure increases as the number of atoms over which a charge is shared increases. A positive charge on a less electronegative atom is more stable than a positive charge on a more electronegative atom. In the acid catalyzed reaction of an ester, the first step in the mechanism is believed to be the protonation of the oxygen atom in the C=O group. The acid catalyzed hydrolysis of an ester converts an ester into a carboxylic acid.

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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 6, Problem 6.65P

Interpretation Introduction

Interpretation:

Based on charge stability, it is be determined why the protonation of the oxygen in the C=O group takes place selectively when there is another oxygen atom that can be protonated.

Concept introduction:

For a proton transfer reaction, the stability of a particular species depends on the following factors in the given order: charge, atom, resonance delocalization, and inductive effects. If protonation occurs at the same atom, then resonance delocalization effects needs to be considered. Stability of a particular structure increases as the number of atoms over which a charge is shared increases. A positive charge on a less electronegative atom is more stable than a positive charge on a more electronegative atom. In the acid catalyzed reaction of an ester, the first step in the mechanism is believed to be the protonation of the oxygen atom in the C=O group. The acid catalyzed hydrolysis of an ester converts an ester into a carboxylic acid.

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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 6, Problem 6.65P

Interpretation Introduction

Interpretation:

Based on charge stability, it is be determined why the protonation of the oxygen in the C=O group takes place selectively when there is another oxygen atom that can be protonated.

Concept introduction:

For a proton transfer reaction, the stability of a particular species depends on the following factors in the given order: charge, atom, resonance delocalization, and inductive effects. If protonation occurs at the same atom, then resonance delocalization effects needs to be considered. Stability of a particular structure increases as the number of atoms over which a charge is shared increases. A positive charge on a less electronegative atom is more stable than a positive charge on a more electronegative atom. In the acid catalyzed reaction of an ester, the first step in the mechanism is believed to be the protonation of the oxygen atom in the C=O group. The acid catalyzed hydrolysis of an ester converts an ester into a carboxylic acid.

Expert Solution & Answer

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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 6, Problem 6.65P

Interpretation Introduction