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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Indicate whether or not each of the salts in Problem 17-72 can be converted back to its “parent” amine through reaction with a strong base.

Chapter 6, Problem 6.74EP, Indicate whether or not each of the salts in Problem 17-72 can be converted back to its parent amine , example  1

Chapter 6, Problem 6.74EP, Indicate whether or not each of the salts in Problem 17-72 can be converted back to its parent amine , example  2

Chapter 6, Problem 6.74EP, Indicate whether or not each of the salts in Problem 17-72 can be converted back to its parent amine , example  3

Chapter 6, Problem 6.74EP, Indicate whether or not each of the salts in Problem 17-72 can be converted back to its parent amine , example  4

(a)

Interpretation Introduction

Interpretation:

“Parent” amine can be regenerated from the given salt or not has to be indicated.

Concept Introduction:

Quaternary ammonium salt is the one that has four carbon atoms attached to the nitrogen atom.  This is formed by the reaction of tertiary amine with alkyl halide in presence of a strong base.

Neutralization reaction is the one that takes place between an acid and a base to give salt as product.  As amines are bases due to the amino group in it, the reaction with inorganic acid or carboxylic acid gives salt as product.  The salt formed is an amine salt.  Proton is donated from the acid to the nitrogen atom which acts as a proton acceptor.  In simple words, it can be said that in an amine‑acid reaction, the acid loses a hydrogen ion and amine gains a hydrogen ion.

When a strong base is added to the amine salt, the parent amine can be obtained.  This is a reverse reaction of the amine salt formation reaction.  These reactions can be represented as shown below,

Organic And Biological Chemistry, Chapter 6, Problem 6.74EP , additional homework tip  1

Quaternary ammonium salt does not give the “parent” amine when treated with a strong base as there is no possibility of deprotonation to take place.

Explanation

If a hydrogen ion is bonded to the nitrogen atom with a positive charge over it it is known as an amine salt.  In quaternary ammonium salt, the nitrogen is bonded to four carbon atoms.  The nitrogen atom in both amine salt and quaternary ammonium salt has a positive charge.  This positive charge is balanced by the negative charge of an acid.

Given structure of salt is,

(b)

Interpretation Introduction

Interpretation:

“Parent” amine can be regenerated from the given salt or not has to be indicated.

Concept Introduction:

Quaternary ammonium salt is the one that has four carbon atoms attached to the nitrogen atom.  This is formed by the reaction of tertiary amine with alkyl halide in presence of a strong base.

Neutralization reaction is the one that takes place between an acid and a base to give salt as product.  As amines are bases due to the amino group in it, the reaction with inorganic acid or carboxylic acid gives salt as product.  The salt formed is an amine salt.  Proton is donated from the acid to the nitrogen atom which acts as a proton acceptor.  In simple words, it can be said that in an amine‑acid reaction, the acid loses a hydrogen ion and amine gains a hydrogen ion.

When a strong base is added to the amine salt, the parent amine can be obtained.  This is a reverse reaction of the amine salt formation reaction.  These reactions can be represented as shown below,

Organic And Biological Chemistry, Chapter 6, Problem 6.74EP , additional homework tip  2

Quaternary ammonium salt does not give the “parent” amine when treated with a strong base as there is no possibility of deprotonation to take place.

(c)

Interpretation Introduction

Interpretation:

“Parent” amine can be regenerated from the given salt or not has to be indicated.

Concept Introduction:

Quaternary ammonium salt is the one that has four carbon atoms attached to the nitrogen atom.  This is formed by the reaction of tertiary amine with alkyl halide in presence of a strong base.

Neutralization reaction is the one that takes place between an acid and a base to give salt as product.  As amines are bases due to the amino group in it, the reaction with inorganic acid or carboxylic acid gives salt as product.  The salt formed is an amine salt.  Proton is donated from the acid to the nitrogen atom which acts as a proton acceptor.  In simple words, it can be said that in an amine‑acid reaction, the acid loses a hydrogen ion and amine gains a hydrogen ion.

When a strong base is added to the amine salt, the parent amine can be obtained.  This is a reverse reaction of the amine salt formation reaction.  These reactions can be represented as shown below,

Organic And Biological Chemistry, Chapter 6, Problem 6.74EP , additional homework tip  3

Quaternary ammonium salt does not give the “parent” amine when treated with a strong base as there is no possibility of deprotonation to take place.

(d)

Interpretation Introduction

Interpretation:

“Parent” amine can be regenerated from the given salt or not has to be indicated.

Concept Introduction:

Quaternary ammonium salt is the one that has four carbon atoms attached to the nitrogen atom.  This is formed by the reaction of tertiary amine with alkyl halide in presence of a strong base.

Neutralization reaction is the one that takes place between an acid and a base to give salt as product.  As amines are bases due to the amino group in it, the reaction with inorganic acid or carboxylic acid gives salt as product.  The salt formed is an amine salt.  Proton is donated from the acid to the nitrogen atom which acts as a proton acceptor.  In simple words, it can be said that in an amine‑acid reaction, the acid loses a hydrogen ion and amine gains a hydrogen ion.

When a strong base is added to the amine salt, the parent amine can be obtained.  This is a reverse reaction of the amine salt formation reaction.  These reactions can be represented as shown below,

Organic And Biological Chemistry, Chapter 6, Problem 6.74EP , additional homework tip  4

Quaternary ammonium salt does not give the “parent” amine when treated with a strong base as there is no possibility of deprotonation to take place.

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