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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: AussieKenDoll on July 16, 2019, 10:18:36 AM

Title: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
Post by: AussieKenDoll on July 16, 2019, 10:18:36 AM
Why Nucleophilic substitution of pyridine undergoes predominantly at C2 and C4 but not on C3, why?
Title: Re: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
Post by: spirochete 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.
Title: Re: Why Nucleophilic substitution of pyridine undergoes at C2 and C4 but not on C3?
Post by: AussieKenDoll 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