In addition to the Kekulé-type contributors to the pyridine resonance hybrid shown on page 391, there are

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In addition to the Kekulé-type contributors to the pyridine resonance hybrid shown on page 391, there are three minor dipolar contributors. Draw their structures. Do they suggest a reason why pyridine is deactivated (relative to benzene) toward reaction with electrophiles and a reason why substitution, when it does occur, takes place at the 3-position?
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Organic Chemistry A Short Course

ISBN: 978-1111425562

13th edition

Authors: Harold Hart, Christopher M. Hadad, Leslie E. Craine, David J. Hart

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