Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Pyrrole undergoes electrophilic aromatic substitution preferentially at the 2 position as
illustrated by the synthesis of 2-nitropyrrole.
CH,COOH
+ HNO3
+ H,O
`NO2
5°C
H
Рyrrole
2-Nitropyrrole
Write resonance contributing structures for the intermediate formed by attack of NO,+
at the 2 and 3 positions of pyrrole. From examination of these intermediates, offer an
explanation for preferential nitration at the 2 position.
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Transcribed Image Text:Pyrrole undergoes electrophilic aromatic substitution preferentially at the 2 position as illustrated by the synthesis of 2-nitropyrrole. CH,COOH + HNO3 + H,O `NO2 5°C H Рyrrole 2-Nitropyrrole Write resonance contributing structures for the intermediate formed by attack of NO,+ at the 2 and 3 positions of pyrrole. From examination of these intermediates, offer an explanation for preferential nitration at the 2 position.
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