ORGANIC CHEMISTRY-EBOOK>I<
ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Chapter 24.SE, Problem 52AP
Interpretation Introduction

Interpretation:

Drawing resonance structures why p-nitroaniline is less basic than m-nitroaniline by a factor of 30 is to be explained. Given that the pKa values of the corresponding ammonium ions are 1.0 and 2.5 respectively.

Concept introduction:

Amines are basic as they can donate the lone pair if electrons on the N atom. The basic strength of amines depends on the availability of lone pair of electrons on nitrogen. Generally aryl amines are less basic than alkyl amines. An electron withdrawing substituent present on the aromatic ring reduces the base strength while an electron releasing substituent present on the aromatic ring enhances the base strength.

To account::

By drawing resonance structures why p-nitroaniline is less basic than m-nitroaniline by a factor of 30. Given that the pKa values of the corresponding ammonium ions are 1.0 and 2.5 respectively.

Answer:

p-Nitroaniline is less basic than m-nitroaniline by a factor of 30 since in p-nitroaniline the nitro group is in conjugation with the amino group and hence resonance delocalization as shown is possible.

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 24.SE, Problem 52AP , additional homework tip  1

In m-nitroaniline such delocalization to nitro group is not possible and only inductive effect operates. Thus m-nitroaniline can donate electron faster than p-nitroaniline. Hence p-nitroaniline is weaker than m-nitroaniline.

Explanation:

The electron withdrawing inductive effect of the nitro group reduces the availability of lone pair of electrons on N of the amino group. But in p-nitroaniline in addition to inductive effect electron delocalization of the lone pair of the amino group in to the nitro group also is possible. In m-nitroaniline such a delocalization to the nitro group is not possible. Thus in comparison, the lone pair on N of the amino group is less available for donation in p-nitroaniline than those in m-nitroaniline. Hence p-nitroaniline is less basic than m-nitroaniline.

Conclusion:

p-Nitroaniline is less basic than m-nitroaniline by a factor of 30 since in p-nitroaniline the nitro group is in conjugation with the amino group and hence resonance delocalization as shown is possible.

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 24.SE, Problem 52AP , additional homework tip  2

In m-nitroaniline such delocalization to nitro group is not possible. Thus m-nitroaniline can donate electron faster than p-nitroaniline. Hence p-nitroaniline is weaker than m-nitroaniline.

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Chapter 24 Solutions

ORGANIC CHEMISTRY-EBOOK>I<

Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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