(a) Interpretation: The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted. Concept introduction: The OH − is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid , the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

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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 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

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(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

fcrip = ↓ bandwidth Il temp 32. What impact (increase, decrease, or no change) does each of the following conditions have on the individual components of the van Deemter equation and consequently, band broadening? Increase temperature Longer column Using a gas mobile phase instead of liquid Smaller particle stationary phase Multiple Paths Diffusion Mass Transfer

34. Figure 3 shows Van Deemter plots for a solute molecule using different column inner diameters (i.d.). A) Predict whether decreasing the column inner diameters increase or decrease bandwidth. B) Predict which van Deemter equation coefficient (A, B, or C) has the greatest effect on increasing or decreasing bandwidth as a function of i.d. and justify your answer. Figure 3 Van Deemter plots for hydroquinone using different column inner diameters (i.d. in μm). The data was obtained from liquid chromatography experiments using fused-silica capillary columns packed with 1.0-μm particles. 35 20 H(um) 큰 20 15 90 0+ 1500 100 75 550 01 02 594 05 μ(cm/sec) 30 15 10

Answer 2

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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 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

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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 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

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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 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

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Answer 5

Chapter 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Answer 6

Chapter 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Answer 7

Chapter 20, Problem 20.5P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn and the overall product(s) of the reaction is to be predicted.

Concept introduction:

The OH− is the nucleophile and attacks the electron poor C of the amide. After nucleophilic-addition and -elimination to produce an initial carboxylic acid, the carboxylic acid is deprotonated irreversibly. Acid workup adds the proton back. The direct formation of the carboxylic acid from the amide is energetically unfavorable due to the negative charge being so poorly stabilized on N in the leaving group. Therefore, the reaction is reversible through the second step. However, the proton transfer in Step 3 is irreversible. It is the critical step that drives the reaction toward products. Without this step, no appreciable amount of product would form.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

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