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Nucleophilic Substitution

  1. Nov 9, 2006 #1
    1) Predict the relative reaction times from fastest to slowest for the following compounds with NaI in acetone: 1-chlorobutane, 1-bromobutane, 2-chlorobutane.

    I am assuming that this is under SN2 reaction conditions with the solvent and compound given.

    2-chlorobutane = secondary substrate = slowest
    1-bromobutane = primary substrate = fastest (Br is larger than Cl)
    1-chlorobutane = primary substrate = moderate rate

    2) Indicate whether the following statements refer to SN1 or SN2 reactions.

    tertiary alcohols - SN1??
    sp2 planar like transition state - SN1?? I am unsure of this one.
    reaction rate independent of the concentration and nature of nucleophile = SN1??
    inversion and retention of stereochemistry - SN2??
    primary and secondary alcohols - SN2???
    carbocation intermediate - SN1 ??

  2. jcsd
  3. Nov 9, 2006 #2
    You are correct in your assumptions. I performed a similar experiment just yesterday for my organic lab.
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