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Trole undergoes nitration by electrophilic aromati

Pyrrole undergoes nitration by electrophilic aromatic substitution. Complete the mechanism by drawing curved arrows, the structure of the charged intermediate, and the structure of the major uncharged product. Omit electron lone pairs and bases.

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NO2 NO 76% 1.5 eq.DMF AcONa 8 1.5 eq. POCl, H2O CH2C2 fux 1 hr. reflux 1-1.5 hr



Pyrrole undergoes electrophilic aromatic substitution predominantly at the 2 and 5 positions. Two such reactions that are especially significant for producing functionalized pyrroles are theMannich reaction and the Vilsmeier-Haack reaction (depicted below), both of which are compatible with a variety of pyrrole substrates

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