NO2 H,SO4 + HNO, + H2O 300°C Pyridine 3-Nitropyridine

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.68P: Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this...
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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.

NO2
H,SO4
+ HNO,
+ H2O
300°C
Pyridine
3-Nitropyridine
Transcribed Image Text:NO2 H,SO4 + HNO, + H2O 300°C Pyridine 3-Nitropyridine
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