To identify which of the given reaction is not feasible. Concept introduction: The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

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Answer 1

Question

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

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Students have asked these similar questions

What is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones? a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water. b. The rate of reaction in base catalyzed process is slower than acid catalyzed process. c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound. d. Only 1 and 3 are correct.

Here in Chapter 19, we learned that converting a ketone or aldehyde to an acetal is a good way to protect the carbonyl group, because an acetal is composed of ether linkages. In Problem 17.57, we saw that a ketone or aldehyde can be converted into an epoxide, which is a cyclic ether. Why would an epoxide be a poor choice as a protecting group?

In paragraph/essay form:Provide an explanation (in detail) on how base catalysts speed up nucleophilic reactions of carbonyl compounds.

Answer 2

Question

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

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Answer 3

Question

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

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Answer 4

Question

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

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Answer 5

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

Answer 6

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

Answer 7

Chapter 15, Problem 63P

(a)

Interpretation Introduction

Interpretation:

To identify which of the given reaction is not feasible.

Concept introduction:

The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.

Concept introduction:

The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.

The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the rate of reaction increases.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3P Ch. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6P Ch. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...

Solution Summary: The author explains that the nucleophilic acyl substitution reaction of carboxylic acid and its derivatives is not feasible.

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