anonymous
  • anonymous
This molecule is a dimer, suggest a possible mechanism for "cracking" the dimer to obtain the original monomer. Have fun!
Organic
jamiebookeater
  • jamiebookeater
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anonymous
  • anonymous
|dw:1441282791073:dw|
anonymous
  • anonymous
Photon336
  • Photon336
wow, oh boy!

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anonymous
  • anonymous
Hahaha any idea, or at least can you identify the monomer that dimerized to form this?
Photon336
  • Photon336
=)
Photon336
  • Photon336
|dw:1441341184394:dw| I guess I don't think it would happen this way because the structure I drew wouldn't predominate b/c carbons octet isn't satisfied. |dw:1441341653269:dw| it's gotta be some kind of radical mechanism @woodward , I think you stumped me, @arindameducationusc hey can you help here?
Photon336
  • Photon336
anonymous
  • anonymous
I'll give another example, maybe this will help. Cyclopentadiene also dimerizes when left sitting out, and the mechanism is a Diels-Alder reaction: https://lh5.googleusercontent.com/89doymsdl_ojvmKmvF4863ihLBzxWnMmV18I8c2qkhbA6r6sAk5wzZr8XI-ekZHbRse5qLkTi16f4tarpKlndquFD_I6bFam_UThxWPmsna0r8_F5XUTUXCko1GW00hqdVM And correspondingly, here's the reverse, cracking it back into the monomers: https://lh3.googleusercontent.com/d9spJz9wzBIfWL_q2xQlKLbvryATTav0aBc9C7HWrUQp94WNCGOOi8jT4rcN3IHKH4DbUZXCvzd4yAE6eFPHZtusgL9Ibf0kp0dfAqDI-SX5DrZkMOlB5ITII8ryh9v0_eA So the dimer is really two of the original monomers fused together! By looking at the dimer in this example, we can see that the molecular formula is \(C_{10}H_{12}\) so the monomer, since it's exactly two stuck together, must be \(C_5H_6\), since I am just dividing by 2. To start taking the first step in "cracking" this problem (terrible pun sadly intended) determine the molecular formula of this lactone (almost an epoxide, but slightly different!), and then divide all the subscripts by 2 to determine the molecular formula of the monomer! That's it! After you do that, then this will at least allow you to try to create some possibilities blindly of what the original monomer might be, so if you can figure out all possible structures for the monomer (which might be surprisingly more challenging than you think) try to do that too and see what you get!
Photon336
  • Photon336
If I remember correctly, the mechanism is like this: one of the cyclopentadiene has to form a structure like this: I'm going to take this step by step woodward please keep this question open. |dw:1441382141800:dw| |dw:1441382320923:dw| |dw:1441382402263:dw| My question is how does the orbital diagram reflect which type of product you get @woodward |dw:1441382838392:dw| |dw:1441383372150:dw|

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