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2010 Destroyer ochem #50

Discussion in 'DAT Discussions' started by fuqele, Mar 3, 2012.

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  1. fuqele

    fuqele

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    Hey guys,

    I'm a little confused about this question. Can somebody help me?

    The question gives a bunch of reactions and ask which one produces alkene. My question is for one of the choices. The reaction is a (Ch3)3-C-I reacting with Ch3OH(aq). I thought that Since Ch3OH is a weak base/nuc and the alkyl halide is tertiary, this could go E1 or SN1, so you get a mixture of both products. The answer says that it only does SN1. Can someone tell me why?

    Thanks in advance. :)
  2. Neil45

    Neil45 Member

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    I think in order to yield an E1 product, you need heat. This isn't shown in choice E (sometimes heat is denoted with a triangle symbol) with the (CH3)3-C-I reacting with methanol.
  3. drejto

    drejto

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    The above post is correct. It is easier to think about it this way though. SN1 requires both a GOOD nucleophile and weak base however and E1 only needs a weak base. This is because the E1 will have the assistance of acid and heat to help to remove the leaving group. Since the question you have says that you have a good nucleophile and weak base, then there is no need for it to go under a E1 reaction.

    http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch08/ch8-9.html
  4. thejamespark

    thejamespark

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    oh yeah i remember this problem.
    you need heat in order to continue a elimination reaction (E1).
  5. fuqele

    fuqele

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    Ahh, got it. Thanks for all the replies!

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