2-methoxypyrrole is brominated exhaustively by treatment with Br2, while 2- methoxypyridine is selectively brominated at the 5-position. Explain the differences in reactivity, and the regioselectivity of the pyridine bromination, using resonance structures as part of your explanation.

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Chapter1: Chemical Foundations
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2-methoxypyrrole is brominated exhaustively by treatment with Br2, while 2-
methoxypyridine is selectively brominated at the 5-position. Explain the
differences in reactivity, and the regioselectivity of the pyridine bromination,
using resonance structures as part of your explanation.

Br
Br
Br2
Br
OMe
OMe
Br.
Br2
OMe
N'
OMe
Transcribed Image Text:Br Br Br2 Br OMe OMe Br. Br2 OMe N' OMe
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