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 .

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Arrange the following substances in order of increasing stability of conjugate base. 1. H₂Se II. H₂S III. H₂ Te || < ||| < | ||| < | < || | < ||| < || O II < | < || O I < || < ||| ||| < || < |

Draw the products of the following proton transfer reaction. Show all unshared electron pairs in your structures. Label the acid and base in the starting materials, and place the conjugate acid and conjugate base products in the appropriate boxes. When drawing a hydrocarbon use a skeletal structure.

Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

Check out a sample textbook solution

See solution

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