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Question
Chemistry
Posted about 1 month ago
why ozazole don't undergo electrophilic substiton
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Answer from Sia
Posted about 1 month ago
Solution
1
Identify the structure of oxazole: Oxazole is a five-membered heterocyclic compound containing one oxygen and one nitrogen atom at positions 1 and 3, respectively. Its structure can be represented as follows: C3H3NO \text{C}_3\text{H}_3\text{NO}
2
Understand electrophilic substitution: Electrophilic aromatic substitution (EAS) is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction typically occurs in benzene and other aromatic compounds due to the delocalized π-electrons that stabilize the intermediate carbocation
3
Analyze the electronic structure of oxazole: In oxazole, the nitrogen atom has a lone pair of electrons, and the oxygen atom is highly electronegative. These atoms withdraw electron density from the ring, making it less electron-rich compared to benzene. This reduced electron density makes the ring less reactive towards electrophiles
4
Consider resonance effects: The lone pair on the nitrogen can participate in resonance, but this delocalization is not as effective as in benzene. The presence of the electronegative oxygen further reduces the electron density on the ring, making the formation of a stable carbocation intermediate less favorable
5
Conclusion: Due to the electron-withdrawing effects of the nitrogen and oxygen atoms, and the less effective resonance stabilization, oxazole is less reactive towards electrophilic substitution reactions compared to benzene and other aromatic compounds
Answer
Oxazole does not undergo electrophilic substitution reactions due to the electron-withdrawing effects of the nitrogen and oxygen atoms, which reduce the electron density on the ring and make the formation of a stable carbocation intermediate less favorable.
Key Concept
Electron-withdrawing effects in oxazole
Explanation
The nitrogen and oxygen atoms in oxazole withdraw electron density from the ring, making it less reactive towards electrophiles and less favorable for electrophilic substitution reactions.

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