EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
4th Edition
ISBN: 9781119659525
Author: Klein
Publisher: WILEY CONS
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Chapter 22, Problem 46PP

(a)

Interpretation Introduction

Interpretation: Hexylamines have to be synthesized from various starting compounds.

Concept Introduction: The general formula for hexylamine is C6H13NH2.  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.

Step-1:  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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  1

Step-2: Formation of R−N bond by SN2 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 SN2 nucleophilic substitution reaction.  Halogen atom is going away as halide anion.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  2

Step-3: 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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  3

(b)

Interpretation Introduction

Interpretation: Hexylamines have to be synthesized from various starting compounds.

Concept Introduction: The general formula for hexylamine is C6H13NH2.  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.

Step-1:  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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  4

Step-2: Formation of R−N bond by SN2 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 SN2 nucleophilic substitution reaction.  Halogen atom is going away as halide anion.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  5

Step-3: 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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  6

(c)

Interpretation Introduction

Interpretation: Hexylamines have to be synthesized from various starting compounds.

Concept Introduction: The general formula for hexylamine is C6H13NH2.  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.

Step-1:  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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  7

Step-2: Formation of R−N bond by SN2 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 SN2 nucleophilic substitution reaction.  Halogen atom is going away as halide anion.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  8

Step-3: 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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  9

(d)

Interpretation Introduction

Interpretation: Hexylamines have to be synthesized from various starting compounds.

Concept Introduction: The general formula for hexylamine is C6H13NH2.  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.

Step-1:  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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  10

Step-2: Formation of R−N bond by SN2 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 SN2 nucleophilic substitution reaction.  Halogen atom is going away as halide anion.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  11

Step-3: 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.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 46PP , additional homework tip  12

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Chapter 22 Solutions

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