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Organic Chemistry - Stereochemistry Problem

Discussion in 'DAT Discussions' started by skyisblue, Feb 24, 2007.

  1. skyisblue

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    What is the stereochemistry of the product that results from addition of Br2 to 1-methylcyclohexene? Is the product optically active? Explain.

    I have the solution to this problem, but I was just wondering if someone can explain it to me in layman's terms.......I'm having a hard time getting this down.....
     
  2. CyborgNinjaX

    CyborgNinjaX Junior Member
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    This is a Markovnikov product because A) anti-markovnikov product would involve hydroboration (BH3). B) the double bond.

    The product is going to be 1-bromo-1-methyl-cyclohexane and hydrobromic acid. My guess is going to be that it is not going to be active.
     
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  3. slashnroses19

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    the carbon 1 that is connected to the methyl group is achiral so it will not be optically active. its connected to two CH2s, a Br, and a CH3. what does your solution say?
     
  4. REH

    REH Junior Member
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    I think it might be 1,2-dibromo-1-methycyclohexane. There's a bromonium ion intermediate and the incoming bromide ion would attack anti to that. If that is the case, I believe it would generate a chiral carbon.
     
  5. OP
    OP
    skyisblue

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    It's a 50:50 racemic mixture of R,R and S,S dibromides with each Br on opposite side. Yeah, these problems are tricky.
     

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