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

Want to see more full solutions like this?

Answer 1

Question

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

Chapter 20.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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 20

Want to see more full solutions like this?

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

Students have asked these similar questions

1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]

humbnai Concentration Terms[1].pdf ox + New Home Edit Sign in Comment Convert Page Fill & Sign Protect Tools Batch +WPS A Free Trial Share Inter Concreting Concentration forms. Hydrogen peroxide is a powerful oxidizing agent wed in concentrated solution in rocket fuels and in dilute solution as a hair bleach. An aqueous sulation of H2O2 is 30% by mass and has density of #liligime calculat the Ⓒmolality ⑥mole fraction of molarity. 20 9. B. A sample of Commercial Concentrated hydrochloric ET

If a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.

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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 20

Want to see more full solutions like this?

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

Answer 3

Question

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

Chapter 20.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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 20

Want to see more full solutions like this?

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

Answer 4

Question

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

Chapter 20.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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 20

Want to see more full solutions like this?

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

Answer 5

Chapter 20.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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 2

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 4

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 7

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 9

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 12

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 14

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 19

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 20.SE, Problem 23MP , additional homework tip 17

Hydrolysis of the amide:

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.