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another orgo question

Discussion in 'DAT Discussions' started by pistolpete007, Jun 13, 2008.

  1. pistolpete007

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    if u have benzylethane and react it with HBr/ROOR.....


    do u get RCH(Br)CH3.....R=benzenegroup

    or do u get RCH2CH2Br

    the reason why i am confused is because if u have benzylethane and react it with Br2,hv or NBS, ROOR, heat....u get RCH(Br)CH3

    HOWEVER if u have methylcyclopentane and react it w/ Br2/hv you get 1-bromo-1-methyl cyclopentane.....however if u react it with HBr/ROOR u get RCH2Br *R=cyclopentane*......

    so thats why im wondering if u were to add HBr/ROOR to benzylethane you would get RCH2CH2Br R=benzenegroup.........

    and just for the hell of it tell me if this is right as well....methylcyclopentane ---NBS, ROOR, heat--->1-bromo-1-methyl cyclopentane (same as Br2/hv)
     
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  3. doc3232

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    I am gonna have to say no reaction.
    ROOR with HBr requires an electrophile (double bond). Only way for that to work.
    Through radical, ROOR initiates and 1 electron comes from the double bond and the other from the Br (which lost one of its 8 electrons during radicalization with ROOR). Then a Hydrogen which has 1 electron on it bonds to the other electron from the double bond.

    basically, you need a double bond for this to happen.
    Actually I can't think of a situation when a double bond is not needed (so the radicals can work).
    Hope this helps :)
     
  4. pistolpete007

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    thanks man....is this right tho methylcyclopentane ---NBS, ROOR, heat--->1-bromo-1-methyl cyclopentane (same as Br2/hv)
     
  5. doc3232

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    Yes, but I don't think you need heat. At least not in my book, but either way that isn't important.
     

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