(a) Interpretation: It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily. Concept introduction: Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below: An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Question

Want to see more full solutions like this?

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 20, Problem 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Students have asked these similar questions

2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

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 20, Problem 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

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 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

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 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 20, Problem 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Answer 6

Chapter 20, Problem 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Answer 7

Chapter 20, Problem 20.5YT

Interpretation Introduction

(a)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Answer 8

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and the reaction does not occur readily.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 2

This is an example of a nucleophilic acyl substitution reaction in which an anhydride is getting converted into an acyl chloride. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 3

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to the one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a lower rung while an acyl chloride is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Answer 13

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Answer 14

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Answer 15

Interpretation Introduction

(b)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Answer 16

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 5

This is an example of a nucleophilic acyl substitution reaction in which an amide is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 6

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an amide is from a lower rung while an ester is from a higher rung on the stability ladder. Thus, this reaction is energetically unfavorable and so does not occur readily.

Answer 21

Conclusion

Conversion of an acid derivative from a lower rung to higher rung on the stability ladder is energetically unfavourable, and the reaction does not occur readily.

Answer 22

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Answer 23

Interpretation Introduction

(c)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Answer 24

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 8

This is an example of nucleophilic acyl substitution reaction in which an acid chloride is getting converted into an ester. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 9

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid chloride is from a higher rung while an ester is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Answer 29

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Answer 30

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Answer 31

Interpretation Introduction

(d)

Interpretation:

It is to be indicated whether the given conversions would be energetically favorable or unfavourable. Also, it is to be given if the reaction is likely to occur readily.

Concept introduction:

Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. An acid derivative has a leaving group, which is substituted by a nucleophile. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Answer 32

Expert Solution

Answer to Problem 20.5YT

The given conversion would be energetically unfavourable, and it does not occur readily.

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The given reaction is

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 11

This is an example of a nucleophilic acyl substitution reaction in which an acid anhydride is getting converted into dicarboxylic acid. If the leaving group is more stable than the nucleophile (weaker in terms of basicity), then the reaction is energetically favorable and occurs readily. If the nucleophile is more stable than the leaving group, then the reaction is enegetically unfavorble and does not occur readilty. This can be explained on the basis of the stability ladder below:

EBK GET READY FOR ORGANIC CHEMISTRY, Chapter 20, Problem 20.5YT , additional homework tip 12

An acyl substitution that converts an acid derivative from a higher rung on the stability ladder to one on a lower rung of the ladder is energetically favorable. An acyl substitution that converts an acid derivative from a lower rung on the stability ladder to one on a higher rung of the ladder is energetically unfavorable.

Referring to this chart, an acid anhydride is from a higher rung while a carboxylic acid is from a lower rung on the stability ladder. Thus, this reaction is energetically favorable and occurs readily.

Answer 37

Conclusion

Conversion of an acid derivative from a higher rung to lower rung on the stability ladder is energetically favourable, and the reaction occurs readily.

Answer 38

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

Concept explainers

Videos

Answer to Problem 20.5YT

Explanation of Solution

Answer to Problem 20.5YT

Explanation of Solution

Answer to Problem 20.5YT

Explanation of Solution

Answer to Problem 20.5YT

Explanation of Solution

Want to see more full solutions like this?

Chapter 20 Solutions