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Which is more stable: a carbocation attached to a methoxy group or a carbocation attached to benzene ring?

Which is more stable: a carbocation attached to a methoxy group or a carbocation attached to benzene ring?

Grade:10

2 Answers

Gaurav
askIITians Faculty 164 Points
6 years ago
Hello Student
Carbocation attached to a benzene ring is highly unstable. This is due to the fact that the benzene ring takes away the electron density from carbon atom which further makes the carbocation unstable.
Shivam Chopra
45 Points
6 years ago
Acc. to me, benzene is a nucleophile & carbocation, as its name suggests, is a cation i.e. it is electrophile. Thus, when an electrophile is attached to benzene, it becomes stable as benzene will give electrons to it & thus, decreasing its charge. That is the reason why electrophilic addition is more preffered in benzene.
For methoxy, although oxygen has a double bond & the methyl group will give electron due to +i effect, but then also, its intensity will be less than benzene.
Thus, benzene will stabilize more charge than methoxy & thus, will be more stable.
Please approve it if you like.

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