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Question
Chemistry
Posted 10 months ago
five membered heterocyclic do not react with electrophiles at heteroatom
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Answer from Sia
Posted 10 months ago
Solution
1
Examine the structure of five-membered heterocycles: Five-membered heterocyclic compounds, such as furan, thiophene, and pyrrole, have a heteroatom (like oxygen, sulfur, or nitrogen) that is part of the ring structure. These heteroatoms possess lone pairs of electrons
2
Understand the reactivity of the heteroatom: The lone pairs on the heteroatom in these heterocycles are involved in the aromatic π-system, which contributes to the aromatic stability of the ring
3
Consider the effect of electrophilic attack: Electrophilic attack at the heteroatom would disrupt the aromatic π-system, leading to a loss of aromatic stability. Therefore, these compounds are less likely to react with electrophiles at the heteroatom
Answer
Five-membered heterocyclic compounds do not typically react with electrophiles at the heteroatom because such a reaction would disrupt their aromatic stability.
Key Concept
Aromatic stability in five-membered heterocycles
Explanation
The lone pairs on the heteroatom of five-membered heterocycles are part of the aromatic π-system, and reacting with electrophiles at the heteroatom would disrupt this stability.

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