Using a Gabriel synthesis, a given primary amine compound has to be synthesized. Concept Introduction : The general formula for primary amine is –NH 2 . There are several methods available to prepare primary amines . Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps. Formation of potassium phthalimide (deprotonation) Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide. Formation of R−N bond by S N 2 nucleophilic substitution The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S N 2 nucleophilic substitution reaction. Halogen atom is going away as halide anion. Formation of primary amine by hydrolysis The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative. To find: Using a Gabriel synthesis, prepare the given primary amine compound Identify the correct alkyl halide involved in the formation of the given compound

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Answer 1

Question

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

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Answer 2

Question

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

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Answer 3

Question

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

Expert Solution & Answer

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Answer 4

Question

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

Expert Solution & Answer

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Answer 5

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

Answer 6

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

Answer 7

Chapter 22.5, Problem 2LTS

Interpretation Introduction

Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.

Concept Introduction:

The general formula for primary amine is –NH₂. There are several methods available to prepare primary amines. Among them, Gabriel synthesis plays a very important role for preparing it. In this method, secondary and tertiary amines are not formed as side products. It involves in three steps.

Formation of potassium phthalimide (deprotonation)

Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.

Formation of R−N bond by S_N2 nucleophilic substitution

The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary alkyl halides (R−X), R and X get positive and negative charges, respectively when they ionize. As a result, a bond between nitrogen of phthalimide and carbon of R is formed. This is S_N2 nucleophilic substitution reaction. Halogen atom is going away as halide anion.

Formation of primary amine by hydrolysis

The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.

To find: Using a Gabriel synthesis, prepare the given primary amine compound

Identify the correct alkyl halide involved in the formation of the given compound

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 22.2 - Prob. 1LTS Ch. 22.2 - Prob. 1PTS Ch. 22.2 - Prob. 2PTS Ch. 22.2 - Prob. 3ATS Ch. 22.3 - Prob. 4CC Ch. 22.3 - Prob. 5CC Ch. 22.3 - Prob. 6CC Ch. 22.3 - Prob. 7CC Ch. 22.3 - Prob. 8CC Ch. 22.3 - Prob. 9CC

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Chapter 22 Solutions