Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.

Question

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Answer 1

Textbook Question

Chapter 20.SE, Problem 25MP

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.

Chapter 20.SE, Problem 25MP, Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

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Answer 2

Textbook Question

Chapter 20.SE, Problem 25MP

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.

Chapter 20.SE, Problem 25MP, Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

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Answer 3

Textbook Question

Chapter 20.SE, Problem 25MP

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.

Chapter 20.SE, Problem 25MP, Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

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Answer 4

Textbook Question

Chapter 20.SE, Problem 25MP

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.

Chapter 20.SE, Problem 25MP, Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

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

Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

Answer 8

Expert Solution

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

a)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 1

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer 13

Answer to Problem 25MP

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 2

Answer 14

Explanation of Solution

In the first step, 2,2-dimethylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2,2-dimethylbutanoic acid.

Answer 15

Conclusion

The products of the reaction are ammonia and 2,2-dimethylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 3

Answer 16

Expert Solution

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Interpretation Introduction

b)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 4

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer 21

Answer to Problem 25MP

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 5

Answer 22

Explanation of Solution

In the first step, p-methylbenzonitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield p-methylbenzoic acid.

Answer 23

Conclusion

The products of the reaction are ammonia and p-methylbenzoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 6

Answer 24

Expert Solution

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Interpretation Introduction

c)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 7

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer 29

Answer to Problem 25MP

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 8

Answer 30

Explanation of Solution

In the first step, 2-methylbutane nitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated aminoketone in the next step and the subsequent proton transfer yields a protonated diol intermediate which eliminates ammonia and a proton in the subsequent steps to yield 2-methylbutanoic acid.

Answer 31

Conclusion

The products of the reaction are ammonia and 2-methylbutanoic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 9

Answer 32

Expert Solution

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.

Conclusion

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 12

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Interpretation Introduction

d)

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 10

Interpretation:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step, is to be given.

Concept introduction:

The acid protonates the nitrogen of the nitrile group initially. The nucleophilic attack by water and subsequent proton transfer will yield an intermediate. Another nucleophilic attack by water on the intermediate and yet another proton transfer produces another intermediate. The intermediate loses ammonia to produce the protonated acid which deprotonates to yield the acid.

To give:

The products of the reaction, the acid-catalyzed nitrile hydrolysis, along with all the steps involved using curved arrows to represent electron flow in each step.

Answer 37

Answer to Problem 25MP

The products of the reaction are ammonia and cyclopentanecarboxylic acid.

The mechanism of the reaction is given below.

Organic Chemistry, Chapter 20.SE, Problem 25MP , additional homework tip 11

Answer 38

Explanation of Solution

In the first step, cyclopentanenitrile is protonated by HCl. In the next step, the nucleophilic attack of water on the protonated nitrile occurs and the accompanying proton transfer yields a protonated aminoketone. Another nucleophilic attack on the carbonyl carbon of the protonated ketone in the next step and the subsequent proton transfer yields a protonated aminodiol intermediate which eliminates ammonia and a proton in the subsequent steps to yield cyclopentanecarboxylic acid.