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Topic: 2-butyliodide + sodium ethanolthiolate = Sn2  (Read 1537 times)

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Offline damib

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2-butyliodide + sodium ethanolthiolate = Sn2
« on: September 29, 2018, 11:15:39 AM »
Hello,
I've been learning for organic chemistry test and I run into this reaction in one workbook 2-butyliodide + sodium ethanolthiolate = Sn2. I assume this is wrong because HS is very strong base, so the reaction will be E2. Am I right? Or why I am not right?
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Offline Babcock_Hall

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Re: 2-butyliodide + sodium ethanolthiolate = Sn2
« Reply #1 on: September 29, 2018, 11:50:09 AM »
Relative base strength can be assessed by finding the pKa of the conjugate acids.  Suppose we compare the conjugate acids of ethanethiolate and ethoxide.  Which conjugate acid is the weaker acid?  Which conjugate base is the weaker base?
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