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Pyridine And Its Reactions
M. Sc. II S.M. Joshi College Prof. Pawar A.A.
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Aromatic Six-Membered-Ring Heterocycles
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Pyridine reacts like a tertiary amine:
The pyridinium ion is a stronger acid than a typical ammonium ion Pyridine reacts like a tertiary amine:
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Pyridine Is Aromatic The nitrogen lone pair is not released into the aromatic system because it is perpendicular to the system. The nitrogen withdraws electrons by resonance, resulting in an electron-deficient ring system.
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Pyridine undergoes electrophilic aromatic substitution at
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The pyridine nitrogen is a meta director:
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Pyridine is reactive toward nucleophilic aromatic substitution because of the presence of the electronegative nitrogen:
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Pyridine undergoes nucleophilic aromatic substitution at
C-2 and C-4:
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If the leaving groups at C-2 and C-4 are different, the
incoming nucleophile will preferentially substitute for the weaker base:
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Bromination and Oxidation of
Substituted Pyridine
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Diazotization of Aminopyridine
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The a-hydrogens of alkyl substituents can be removed by base to generate anionic nucleophiles:
Pyridine a-hydrogen acidity is similar to that of ketone a-hydrogens
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Quinoline and isoquinoline are ring-fused pyridine derivatives:
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Reactions of pyridine-based anionic nucleophiles:
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