OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Question
Chapter 22, Problem 22.8P
Interpretation Introduction
Interpretation:
Reason for the preferential of nitration of pyridine at 3rd position has to be given and also resonance contributors for the intermediate formed by attack of
Expert Solution & Answer
Explanation of Solution
Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.
For nitration at the 2nd position or 4th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3rd position.
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Pyridine undergoes electrophilic aromatic substitution preferentially at the 3 position as illustrated by the synthesis of 3-nitropyridine.
Under these acidic conditions, the species undergoing nitration is not pyridine, but its conjugate acid. Write resonance contributing structures for the intermediate formed by attack of NO2+ at the 2, 3, and 4 positions of the conjugate add of pyridine. From examination of these intermediates, offer an explanation for preferential nitration at the 3 position.
Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4.
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Chapter 22 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
Ch. 22.1 - Prob. 22.1PCh. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3PCh. 22.2 - Prob. 22.4PCh. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...
Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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