ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<
ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<
4th Edition
ISBN: 9781119850151
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 51PP

(a)

Interpretation Introduction

Interpretation: The difference in basicity between ortho- or para- and meta-nitroanilines has to be discussed

Concept Introduction:

Resonance is a mental exercise and method within the Valence Bond Theory of bonding that describes the delocalization of electrons within molecules.  The net sum of valid resonance structures is defined as a resonance hybrid, which represents the overall delocalization of electrons within the molecule.  A molecule that has several resonance structures is more stable than one with fewer.  If the delocalization of electrons within molecules is more, the compound is less basic and vice versa.

To find: para-nitroaniline is an order of magnitude less basic than meta-nitroaniline.  Find the reason for the given statement

Find the delocalization behavior of para-nitroaniline

ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<, Chapter 22, Problem 51PP , additional homework tip  1

(b)

Interpretation Introduction

Interpretation: The difference in basicity between ortho- or para- and meta-nitroanilines has to be discussed

Concept Introduction:

Resonance is a mental exercise and method within the Valence Bond Theory of bonding that describes the delocalization of electrons within molecules.  The net sum of valid resonance structures is defined as a resonance hybrid, which represents the overall delocalization of electrons within the molecule.  A molecule that has several resonance structures is more stable than one with fewer.  If the delocalization of electrons within molecules is more, the compound is less basic and vice versa.

To find: Finding the basicity of ortho-nitroaniline which is closer in value to meta- or to para-nitroaniline

Find the delocalization behavior of ortho-nitroaniline

ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<, Chapter 22, Problem 51PP , additional homework tip  2

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Chapter 22 Solutions

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