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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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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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