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Homework Help: Organic chemistry SN1 reaction's

  1. Oct 22, 2008 #1
    1. The problem statement, all variables and given/known data

    Find the major organic product B of http://www.webassign.net/userimages/kasandbe/CH221_ssii_02/CH221_exam2_ssii_02_7a.gif

    (with ethanol at 0 degrees Celsius)
    2. Relevant equations

    3. The attempt at a solution

    I thought that since it is a SN1 reaction the -OTs would be the LG and that -OCH2CH3 would connect to the carbon it was on and form a racemic mixture but this isn't the right answer can anyone clear this up I seem to be confused? Thanks.
  2. jcsd
  3. Oct 23, 2008 #2


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    That's certainly possible but only as a minor product. You will note that in this SN1 reaction, OTs- is indeed the leaving group. Study the carbonium ion that results. It is a secondary carbonium ion next to a 3o carbon and a 1o carbon. What might happen?
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