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Cycloalkene Chlorination w/ Dichloromethane?

  1. Oct 11, 2010 #1
    1. The problem statement, all variables and given/known data

    I am currently working on a homework assignment in Bruice Organic Chemistry and have ran across a problem that I can't find an answer to anywhere. It is simply a reaction between cyclopentane and chlorine in the presence of dichloromethane.

    2. Relevant equations

    This is in the same chapter that we are looking at reactions such as alkane chlorination with heat or light, and NBS reactions to alkenes. The book doesn't, however, say anything about this reaction between chlorine and a cycloalkane in the presence of DCM. We have, in previous chapters, looked at halogenation of alkene and alkynes in the presence of DCM, but never an alkane or cycloalkane.
    I checked all over the internet and cannot find anything except a few things saying alkanes will only react through halogenation with energy, and combustion, although I myself remember seeing a reaction or two that made alkenes from alkanes.

    3. The attempt at a solution

    If I had to guess, I would say that It would break the chain and add Cl to each side, although this is merely a guess and is not supported by any evidence. It could also behave similar to hydrogenation with energy present.

    Anyways thanks for your help,
  2. jcsd
  3. Sep 1, 2015 #2
    I'm fairly sure there is no reaction. Dichloromethane simply acts as a solvent here, and nothing else is present to act as a radical initiator.
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