a) Interpretation: The products of the reaction along with the mechanism of the reaction are to be given. Concept introduction: The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia. To give: The products of the reaction along with the mechanism of the reaction.

Question

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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.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

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SYNTHESIS REACTIONS. For the following reactions, synthesize the given products from the given reactants. Multiple reactions/steps will be needed. For the one of the steps (ie reactions) in each synthesis, write out the mechanism for that reaction and draw an energy diagram showing the correct number of hills and valleys for that step's mechanism. CI b. a. Use acetylene (ethyne) and any alkyl halide as your starting materials Br C. d. "OH OH III. OH

Calculate the pH and the pOH of each of the following solutions at 25 °C for which the substances ionize completely: (a) 0.200 M HCl

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.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 20.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

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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.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

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Answer 5

Chapter 20.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

Answer 6

Chapter 20.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Answer 7

Chapter 20.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer 8

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 3

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Answer 13

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 5

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Answer 14

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Answer 15

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer 16

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 8

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Answer 21

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 10

Answer 22

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Answer 23

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer 24

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 13

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Answer 29

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 15

Answer 30

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 20

Answer 31

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer 32

Expert Solution

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 23MP , additional homework tip 18

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.