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Organic Chemistry - Elimination/substitution

  1. Mar 13, 2015 #1
    1. The problem statement, all variables and given/known data
    I have this problem:
    I known that reaction with TsOH would replace -OH groups with TsO (substitution reaction). (Et)3N would therefore act as a base to abstract H to form an alkene. The problem is i know it should be an E1cb reaction but how do I obtain an alkene? I tried to draw the mechanism but comes to no solution can anyone help or am i in the wrong direction?
    Compound A would then react with LDA - which I guess is to form alkyne so A should be an alkene) or am I worng?
    Thank you!
    2. Relevant equations
    9stg0p.jpg
    CH3SO2Cl is a good substitution for OH. Et3N is a good base.

    3. The attempt at a solution
    (See part 1) Would the compound form be this: I guess not since the compound is relatively unstable
    upload_2015-3-13_15-19-15.png
     

    Attached Files:

    Last edited: Mar 13, 2015
  2. jcsd
  3. Mar 18, 2015 #2
    Thanks for the post! This is an automated courtesy bump. Sorry you aren't generating responses at the moment. Do you have any further information, come to any new conclusions or is it possible to reword the post?
     
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