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Dienophile and diene help? organic chemistry

  1. Feb 19, 2012 #1
    dienophile and diene help?? organic chemistry

    We never really covered how to do diels alder reactions and im having trouble how
    to do these. Here is a photo of the lab page with the questions. I just need help
    with 2a-e and 3b-3d. Thanks.

    lab12004001.jpg
     
  2. jcsd
  3. Feb 19, 2012 #2

    Borek

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  4. Feb 19, 2012 #3
    Re: dienophile and diene help?? organic chemistry

    Wikipedia doesnt help tried that already.
     
  5. Feb 20, 2012 #4

    Borek

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    Re: dienophile and diene help?? organic chemistry

    Diels-Alder reaction is between two specific structural elements, can you name them? Can you locate them in the compounds listed in the book? It is pretty straightforward.
     
  6. Feb 21, 2012 #5

    chemisttree

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    Re: dienophile and diene help?? organic chemistry

    Start with 2a, can you identify the diene?
     
  7. Feb 21, 2012 #6
    Re: dienophile and diene help?? organic chemistry

    yeah the diene and dienophile.

    2a the diene is the double bonded hexyl groups. The dienophile is the two bonded COOCH3 groups.

    2b. the diene is the cyclehexen-1,3-diene. the dienophile is the 1,2-chlorohexene

    2c. the diene is cyclopenten-1,3-diene. the dienophile is the second one. barely learning to naming those. I know its an ester group.

    2d. the diene is the cyclopenten-1,3-diene. the dienophile is the prop-1-en-2-ol

    2e. the diene is the alkene(2nd compound) and the dienophile is the cyclopentene with the chlorides surrounding it.
     
  8. Feb 21, 2012 #7
    Re: dienophile and diene help?? organic chemistry

    here are my answers

    2a.
     

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  9. Feb 22, 2012 #8

    Borek

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    Re: dienophile and diene help?? organic chemistry

    Close to correct, but you need to think about stereochemistry. Are -COOCH3 on the same side of the ring (they don't lie on the paper surface)?
     
  10. Feb 22, 2012 #9
    Re: dienophile and diene help?? organic chemistry

    oh its both stereocenters so one will have a wedge while the other will have dashed lines
     
  11. Feb 22, 2012 #10
    Re: dienophile and diene help?? organic chemistry

    so something like this?
     

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  12. Feb 22, 2012 #11
    Re: dienophile and diene help?? organic chemistry

    here is my answer for 2b,2c,2d
     

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  13. Feb 22, 2012 #12
    Re: dienophile and diene help?? organic chemistry

    and 2e.
     

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  14. Feb 22, 2012 #13

    Borek

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    Re: dienophile and diene help?? organic chemistry

    2a looks OK to me. Other products will be polycyclic. Dienophile and diene create a new ring (dienophile "closes" the diene).
     
  15. Feb 22, 2012 #14
    Re: dienophile and diene help?? organic chemistry

    so the rest are wrong then? ok ill try to figure them out then
     
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