N,N-Dimethylaniline and pyridine are similar in basicity, whereas

Organic Chemistry, | 9th Edition | ISBN: 9780073402741 | Authors: Francis A Carey Dr., Robert M. Giuliano

Problem 21.53 Chapter 21

Organic Chemistry, | 9th Edition

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Organic Chemistry, | 9th Edition | ISBN: 9780073402741 | Authors: Francis A Carey Dr., Robert M. Giuliano

Organic Chemistry, | 9th Edition

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Problem 21.53

N,N-Dimethylaniline and pyridine are similar in basicity, whereas 4-(N,Ndimethylamino)pyridine is considerably more basic than either. N(CH3)2 N,N-Dimethylaniline pKa of conjugate acid 5.1 N Pyridine pKa of conjugate acid 5.3 N N(CH3)2 4-(N,N-Dimethylamino)pyridine pKa of conjugate acid 9.7 Apply resonance principles to identify the more basic of the two nitrogens of 4-(N,N-dimethylamino)pyridine, and suggest an explanation for its enhanced basicity.

Step-by-Step Solution:
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Chapter 1 2510 IV. (Section 1-4)Lewis Structures A. Rules 1. Draw the desired molecular skeleton CH 4 H H C H H 2. Determine number of valence electrons - - H 4 x 1e = 4e C 1 x 4e = 4e total 8e - 3. Octet rule....

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Chapter 21, Problem 21.53 is Solved
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Textbook: Organic Chemistry,
Edition: 9
Author: Francis A Carey Dr., Robert M. Giuliano
ISBN: 9780073402741

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