Benzene ring question...

[The North Face]

Do any of you know if a double bond in a benzene ring is basic enough to open an epoxide?

Thanks

---

Members don't see this ad.

 

[mychelle774]

Do any of you know if a double bond in a benzene ring is basic enough to open an epoxide?

Thanks

I would say no way. Benzene's double bonds are what make it so stable.

 

[Sol Rosenberg]

Do any of you know if a double bond in a benzene ring is basic enough to open an epoxide?

Thanks

1. A benzene ring has no double bonds.
2. Benzene rings are very stable because of their aromaticity. They will generally not react in any way that disrupts their aromaticity.
3. I'm not sure if epoxides can undergo electrophilic aromatic substitution -- I think that under the right conditions, oxirane could break and form an ethoxy substituent on the ring, but I don't know for sure. This would have nothing to do with the basicity of the ring, however.

 

[Orthodoc40]

That's a question for Q of Q for sure!

 

[Mr. Tee]

too bad aromaticity won't be on the test unless everything was explicitly laid out for you.

 

[OctoDoc]

No.

Technically, your question should have been, Is a double bond of benzene nucleophilic enough to open an epoxide?

(from a former O-Chem professor)