Diels-Alder Polymerization

[BlackSails]

When you do the diels alder reaction (ethene and 1,3 butadiene), you end up with a cyclohexene ring. This ring is a ene. Why does it not undergo another diels alder reaction, forming two fused rings? And that ring is also a ene, so it should react again, etc, and make long polymers of cyclohexane rings, ending with a cyclohexene.

Obviously, there are concentration issues, but those could be easily overcome by using an excess of diene. Does this reaction continue and its just usually competed out, or is there some reason it doesnt happen?

Orbitals on the 1,3 butadiene are HOMO=++--, LUMO=+--+. Orbitals on the cyclohexene are HOMO=++, LUMO=+-. HOMO+LUMO gives bonding interactions in both cases.

---

Members don't see this ad.

 

[MilkmanAl]

You just gave me a brain cramp.

 

[175961]

SDN is not the place to get help with your homework. Closing.


shoot.....I have no real power

 

[bigDee]

When you do the diels alder reaction (ethene and 1,3 butadiene), you end up with a cyclohexene ring. This ring is a diene.

No it isn't. Why would you make a thread on this when you haven't even studied it for more than 5min?

Edit: Actually, I think I see what you're saying. Are you saying why doesn't the 1,3 butadiene react with the cyclohexene? I was confused because you said the ring is a diene, which it isn't because it only has one double bond.

 

[BlackSails]

SDN is not the place to get help with your homework. Closing.


shoot.....I have no real power

Yeah, problem sets due 2 days before a final.

No it isn't. Why would you make a thread on this when you haven't even studied it for more than 5min?

Its a simple typo.

Actually, I think I see what you're saying. Are you saying why doesn't the ethene react with the cyclohexene?

No, the cyclohexene should react with the 1,3 butadiene.

 

[HumidBeing]

SDN is not the place for homework help. Closing.