Chapter 22.3, Problem 6CC

(a)

Interpretation Introduction

Interpretation: The more basic amine compound has to be found for the given pairs of compounds

Concept Introduction:

If the lone pair of electrons on nitrogen atom in amine compound is delocalized, that compound is resonance stabilized.  It is also involved in aromatic stabilization.  As a result, a number of resonance structures are drawn for the delocalization of electrons in the structures.  So, the compound has less basic character.  If the lone pair of electrons on nitrogen atom in amine compound is localized, that compound doesn’t involve in resonance stabilization.  So, that compound has more basic character.

To find: Decide the more basic amine compound in the given pairs of compounds (a)

Get a compound where lone pairs on nitrogen atoms are delocalized

 (b)

Interpretation Introduction

Interpretation: The more basic amine compound has to be found for the given pairs of compounds

Concept Introduction:

If the lone pair of electrons on nitrogen atom in amine compound is delocalized, that compound is resonance stabilized.  It is also involved in aromatic stabilization.  As a result, a number of resonance structures are drawn for the delocalization of electrons in the structures.  So, the compound has less basic character.  If the lone pair of electrons on nitrogen atom in amine compound is localized, that compound doesn’t involve in resonance stabilization.  So, that compound has more basic character.

To find: Decide the more basic amine compound in the given pairs of compounds (b)

Get a compound where lone pairs on nitrogen atoms are delocalized

 (c)

Interpretation Introduction

Interpretation: The more basic amine compound has to be found for the given pairs of compounds

Concept Introduction:

If the lone pair of electrons on nitrogen atom in amine compound is delocalized, that compound is resonance stabilized.  It is also involved in aromatic stabilization.  As a result, a number of resonance structures are drawn for the delocalization of electrons in the structures.  So, the compound has less basic character.  If the lone pair of electrons on nitrogen atom in amine compound is localized, that compound doesn’t involve in resonance stabilization.  So, that compound has more basic character.

To find: Decide the more basic amine compound in the given pairs of compounds (c)

Get a compound where lone pairs on nitrogen atoms are delocalized

(d)

Interpretation Introduction

Interpretation: The more basic amine compound has to be found for the given pairs of compounds

Concept Introduction:

If the lone pair of electrons on nitrogen atom in amine compound is delocalized, that compound is resonance stabilized.  It is also involved in aromatic stabilization.  As a result, a number of resonance structures are drawn for the delocalization of electrons in the structures.  So, the compound has less basic character.  If the lone pair of electrons on nitrogen atom in amine compound is localized, that compound doesn’t involve in resonance stabilization.  So, that compound has more basic character.

To find: Decide the more basic amine compound in the given pairs of compounds (d)

Get a compound where lone pairs on nitrogen atoms are delocalized