The use of amine synthesis for the conversion of allybromide to allylamine is to be shown. Concept introduction: The Gabriel synthesis is used for the preparation of primary amines . It is also called Gabriel phthalimide synthesis. In this synthesis N − alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

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Answer 1

Question

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

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Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions. (c) 1@bromo@3@phenylheptane S 3@phenylheptan@1@amine (d) 1@bromo@3@phenylheptane S 4@phenyloctan@1@amine

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions.(a) allyl bromide S allylamine (b) ethylbenzene S p@ethylaniline

Why do you wash the dichloromethane solution of your reductive amination product with sodium bicarbonate, rather than dilute aqueous HCl? a) Sodium bicarbonate is a good method of removing aldehydes from organic solvent.b) The amine product will be protonated by acid and remain in the aqueous layer as a salt.c) Sodium bicarbonate transfers the amine starting material into the aqueous layer.d) Sodium bicarbonate reacts with leftover NaBH(OAc)3 and removes it from the mixture.

Answer 2

Question

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

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Answer 3

Question

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

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Answer 4

Question

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

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Answer 5

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 6

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 7

Chapter 19, Problem 19.48SP

(a)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of allybromide to allylamine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of ethylbenzene to p-ethylaniline is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 3-phenylheptan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The use of amine synthesis for the conversion of 1-bromo-3-phenylheptane to 4-phenyloctan-1-amine is to be shown.

Concept introduction:

The Gabriel synthesis is used for the preparation of primary amines. It is also called Gabriel phthalimide synthesis. In this synthesis N− alkylated potassium or sodium salt of phthalimide is hydrolysed with alkalies. Such alkaline hydrolysis results in corresponding primary amine.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 19.2A - Prob. 19.1P Ch. 19.2B - Prob. 19.2P Ch. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4P Ch. 19.4 - Prob. 19.5P Ch. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7P Ch. 19.8C - Prob. 19.8P Ch. 19.8C - Prob. 19.9P Ch. 19.8D - a. Show how fragmentation occurs to give the base...

Solution Summary: The author explains the Gabriel synthesis, which is used for the preparation of primary amines.

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Chapter 19 Solutions