(a) Interpretation: Whether t e r t − butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated. Concept introduction: The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine . The reaction is followed by hydrolysis. The reaction follows S N 2 mechanism.

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Answer 1

Question

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

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Answer 2

Question

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

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Answer 3

Question

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

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Answer 4

Question

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

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Answer 5

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

Answer 6

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Answer 7

Chapter 23, Problem 23.38P

Interpretation Introduction

(a)

Interpretation:

Whether tert−butylamine can be prepared using Gabriel synthesis or not is to be stated. If yes, its mechanism is to be stated. If not, the reason corresponding to the answer is to be stated.

Concept introduction:

The Gabriel synthesis involves the reaction between an alkyl halide and phthalimide to convert the alkyl halide into a primary amine. The reaction is followed by hydrolysis. The reaction follows SN2 mechanism.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The synthesis of the compound tert−butylamine is to be stated.

Concept introduction:

The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains that the compound tert-butylamine cannot be prepared using the Gabriel synthesis since it is a hindered molecule.

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Chapter 23 Solutions