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Ochem problem

Discussion in 'DAT Discussions' started by allstardentist, Jul 20, 2006.

  1. allstardentist

    allstardentist All-Star
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    The reaction of 2-chloro-2- methylhexane with sodium cyanide in ethanol results in

    a. the retention of absolute config.
    b. the formation of a racemic mixture
    c. .....
    d. ...
    e. the formation of optically inactive products.

    It seems like the reactant will go through SN1 reaction by the info. given. Doesn't that mean the answer will be either B or E? I put B and the solution is E. Can anyone explain? Thanks
     
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  3. allstardentist

    allstardentist All-Star
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    oh nm.. the reactant doesnt have any stereocenter.im stupid
     
  4. keibee82

    keibee82 Blue_tooth...
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    This will go E2 reaction. CN- is strong nucleophile(base) but substrate is tertiary Sn2 is not possible.
    Therefore only choice is E2 and since the product of E2 will be alkene, its optically inactive.
     

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