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Question
Chemistry
Posted 8 months ago
why pyrrole very resistant to nucleophilic addition and substitution
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Answer from Sia
Posted 8 months ago
Solution
1
Aromaticity: Pyrrole is an aromatic compound, meaning it has a conjugated system of π\pi electrons that are delocalized over the ring. This delocalization provides extra stability to the molecule
2
Electron Density: The nitrogen atom in pyrrole donates its lone pair of electrons to the aromatic system, increasing the electron density within the ring. This makes the ring less electrophilic and less likely to attract nucleophiles
3
Steric Hindrance: The structure of pyrrole creates a certain level of steric hindrance, which can further inhibit nucleophilic addition and substitution reactions
Answer
Pyrrole is very resistant to nucleophilic addition and substitution due to its aromaticity, increased electron density from nitrogen's lone pair, and steric hindrance.
Key Concept
Aromaticity and electron density in pyrrole
Explanation
Pyrrole's aromatic nature and the electron-donating effect of nitrogen's lone pair make the ring less reactive towards nucleophiles. Additionally, steric hindrance plays a role in its resistance to these reactions.

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