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Orgo, destroyer

JDHK

Full Member
Jun 20, 2013
52
0
  1. Pre-Dental
    In this mechanism, I was thinking the bromine would attach itself to the para position due to the ethyl group being a donating group. Why is it that it's attached to the carbon (shown in attachment). Does Br2 and light always attach to allylic carbon?
     

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    ChrisM07

    Dental Student
    10+ Year Member
    Apr 8, 2007
    567
    87
    1. Dental Student
      When you see this: Br2 with light, think free radical halogenation. In this case, ortho/para/meta designations will be irrelevant. The only thing here that can be affected by by free radical halogenation is the ethyl group. Like always, add the Br to the most substituted carbon (unless you reacted Br2 with a peroxide, like ROOR. Then you would add the Br to the LEAST substituted carbon).

      Also, don't forget to look for any kind of shifting that would give a better, more stable carbocation. For instance, if you had a propane group attached instead of methyl, the propane would shift to give a more stable carbocation (tertiary) instead of secondary.
       
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