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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

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

Which of the four terms free amine, free base, deprotonated base, and protonated base apply to each of the following amine species? More than one term may apply in a given situation.

  1. a. CH3—CH2—CH2—NH2
  2. b. CH 3 CH 2 CH 2 N + H 2 CH 3
  3. c. CH 3 NH CH 2 CH 3
  4. d. CH 3 CH 2 N + H 3

(a)

Interpretation Introduction

Interpretation:

The terms that apply for CH3CH2CH2NH2 has to be given.

Concept Introduction:

Free amine is the one that has nitrogen atom bonded to three other atoms and a lone pair of electrons is present on it.  Deprotonated base is the one that can accept a hydrogen ion.  Due to the lone pair of electrons present on the nitrogen atom in amine, it can also be known as deprotonated base.  Free base is the one that has a more electronegative atom which can act as a proton acceptor.  Amine has a nitrogen atom which can accept a hydrogen ion.  Hence, amine can be a proton acceptor.  Protonated base is the one in which the nitrogen atom in the amine has four bonds.  The fourth bond formed is a coordinate covalent bond.  The formed species has a positive charge on it.

Explanation

Given amine is CH3CH2CH2NH2.

On looking into the structure it is found that it has a free amine group present in it

(b)

Interpretation Introduction

Interpretation:

The terms that apply for CH3CH2CH2N+H2CH3 has to be given.

Concept Introduction:

Free amine is the one that has nitrogen atom bonded to three other atoms and a lone pair of electrons is present on it.  Deprotonated base is the one that can accept a hydrogen ion.  Due to the lone pair of electrons present on the nitrogen atom in amine, it can also be known as deprotonated base.  Free base is the one that has a more electronegative atom which can act as a proton acceptor.  Amine has a nitrogen atom which can accept a hydrogen ion.  Hence, amine can be a proton acceptor.  Protonated base is the one in which the nitrogen atom in the amine has four bonds.  The fourth bond formed is a coordinate covalent bond.  The formed species has a positive charge on it.

(c)

Interpretation Introduction

Interpretation:

The terms that apply for CH3NHCH2CH3 has to be given.

Concept Introduction:

Free amine is the one that has nitrogen atom bonded to three other atoms and a lone pair of electrons is present on it.  Deprotonated base is the one that can accept a hydrogen ion.  Due to the lone pair of electrons present on the nitrogen atom in amine, it can also be known as deprotonated base.  Free base is the one that has a more electronegative atom which can act as a proton acceptor.  Amine has a nitrogen atom which can accept a hydrogen ion.  Hence, amine can be a proton acceptor.  Protonated base is the one in which the nitrogen atom in the amine has four bonds.  The fourth bond formed is a coordinate covalent bond.  The formed species has a positive charge on it.

(d)

Interpretation Introduction

Interpretation:

The terms that apply for CH3CH2N+H3 has to be given.

Concept Introduction:

Free amine is the one that has nitrogen atom bonded to three other atoms and a lone pair of electrons is present on it.  Deprotonated base is the one that can accept a hydrogen ion.  Due to the lone pair of electrons present on the nitrogen atom in amine, it can also be known as deprotonated base.  Free base is the one that has a more electronegative atom which can act as a proton acceptor.  Amine has a nitrogen atom which can accept a hydrogen ion.  Hence, amine can be a proton acceptor.  Protonated base is the one in which the nitrogen atom in the amine has four bonds.  The fourth bond formed is a coordinate covalent bond.  The formed species has a positive charge on it.

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