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Topic: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?  (Read 1382 times)

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Offline AussieKenDoll

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Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
« on: July 16, 2019, 10:18:36 AM »
Why Nucleophilic substitution of pyridine undergoes predominantly at C2 and C4 but not on C3, why?
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Offline spirochete

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Re: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
« Reply #1 on: July 16, 2019, 06:38:18 PM »
Draw the mechanism, including all resonance structures for the anionic intermediate. Then, think about them. Where is negative charge more stable in anions? That will explain it.
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Offline AussieKenDoll

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Re: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
« Reply #2 on: July 19, 2019, 11:20:05 AM »
the positive charge is on C2, C4 and C6 on the resonance structures? but I still do not understand why
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