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Organic Chemistry - Elimination/substitution

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Homework Statement


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!

Homework Equations


9stg0p.jpg

CH3SO2Cl is a good substitution for OH. Et3N is a good base.

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
 

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Answers and Replies

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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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