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Question
Chemistry
Posted 10 months ago
why pyrrole very resistant to nucleophilic addition and substitution
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Answer from Sia
Posted 10 months ago
Solution
1
Aromatic Stability: Pyrrole is an aromatic compound, which means it has a cyclic, planar structure with a delocalized π\pi-electron system that follows Hückel's rule of 4n+2 π\pi-electrons
2
Electron Density: The lone pair of electrons on the nitrogen atom in pyrrole is part of the aromatic π\pi-electron system, which increases the electron density of the ring and makes it less susceptible to attack by nucleophiles
3
Reactivity: Due to its aromaticity, pyrrole prefers to undergo electrophilic substitution reactions rather than nucleophilic addition or substitution, which would disrupt its aromatic system
Answer
Pyrrole is resistant to nucleophilic addition and substitution because its aromaticity increases electron density and stabilizes the ring, making it less reactive towards nucleophiles.
Key Concept
Aromaticity and electron delocalization in pyrrole
Explanation
Pyrrole's aromatic nature and the involvement of the nitrogen's lone pair in the delocalized π\pi-electron system make it less reactive to nucleophilic attacks.

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