The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation. Concept introduction: Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate. In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide. Hofmann elimination: Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination. In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

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Answer 1

Question

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

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Early organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.

Primary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primary amine using an alkyl halide and ammonia?

When acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?

Answer 2

Question

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

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Answer 3

Question

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

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Answer 4

Question

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

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Answer 5

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 6

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 7

Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5P Ch. 10.1 - Prob. 6P Ch. 10.1 - Prob. 8P Ch. 10.2 - Prob. 9P Ch. 10.3 - Prob. 11P Ch. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P

Solution Summary: The author explains that the primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

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Chapter 10 Solutions