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anonymous

  • one year ago

In attempting to synthesize cyclohexane from benzene, they somehow got methylcyclopentane. Can anyone write out probable steps going from benzene to methylcyclopentane with HI at 275 degrees C? https://upload.wikimedia.org/wikipedia/commons/d/d9/CyclohexaneBerthelot.svg https://en.wikipedia.org/wiki/Cyclohexane#Early_failures

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  1. anonymous
    • one year ago
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    This should be reaction of rearrangement. In the first place, you add H+, and you for a carbo cataion, and as the structure now is instable, when you rise up the T, it shoud break and rearrange in more stable way.

  2. anonymous
    • one year ago
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    But HI works also ad a reducent agent 2HI--> I2 + H2, where H2 will also make weaker all the structure. So that's why u cant use another acid as HBr or HCl, cuz of their redox potential.

  3. anonymous
    • one year ago
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    Oh, so does that mean HI has a high redox potential and HBr and HCl have a low redox potential?

  4. anonymous
    • one year ago
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    Try to think about the eletconegativity: for Clorine use to riduce a lot, Br little bit less, and I has pretty low tendence to reduce, so it easyer for I to get reoxidated, while i think you will be in touble if you will try to reoxidate Cl- in Cl2

  5. Photon336
    • one year ago
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    I would like to see the mechanism for this step by step.

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