ORGANIC CHEMISTRY WITH WILEY PLUS; ORGAN
ORGANIC CHEMISTRY WITH WILEY PLUS; ORGAN
4th Edition
ISBN: 9781119493426
Author: Klein
Publisher: WILEY
Question
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Chapter 22, Problem 36PP

(a)

Interpretation Introduction

Interpretation: The stronger base has to be identified in the given pair 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.  sp3 hybridized nitrogen atom is expected to function as more basic character than sp2 hybridized nitrogen atom which has again basic character than sp hybridized nitrogen atom.

To find: Identify the stronger base in the given pair of compounds (a)

Find the behavior of nitrogen atom in pyridine

(b)

Interpretation Introduction

Interpretation: The stronger base has to be identified in the given pair 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.  sp3 hybridized nitrogen atom is expected to function as more basic character than sp2 hybridized nitrogen atom which has again basic character than sp hybridized nitrogen atom.

To find: Identify the stronger base in the given pair of compounds (b)

Find the behavior of nitrogen atom in an amide group

(c)

Interpretation Introduction

Interpretation: The stronger base has to be identified in the given pair 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.  sp3 hybridized nitrogen atom is expected to function as more basic character than sp2 hybridized nitrogen atom which has again basic character than sp hybridized nitrogen atom.

To find: Identify the stronger base in the given pair of compounds (c)

Find the behavior of nitrogen atom in five-membered ring

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Chapter 22 Solutions

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