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Topic: sulfonates in nucleophilic substitutions  (Read 5400 times)

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myelver10

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sulfonates in nucleophilic substitutions
« on: November 18, 2004, 06:10:34 PM »
which halide ion would react the fastest with cyclopentyl p-toluenesulfonate in ethanol/water?  would it be I-  Br- Cl- or F-      I was thinking I- since it reacts fastest in an sn2 reaction     but not really sure ???


                                                thanks
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dexangeles

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Re:sulfonates in nucleophilic substitutions
« Reply #1 on: November 20, 2004, 02:45:27 AM »
I'm not 100 positive but if it is a nucleophilic attack then I is always the most reactive
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Offline Donaldson Tan

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Re:sulfonates in nucleophilic substitutions
« Reply #2 on: November 21, 2004, 09:47:08 AM »
Isn't the C-I bond very weak?
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Offline Mitch

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Re:sulfonates in nucleophilic substitutions
« Reply #3 on: November 21, 2004, 04:07:22 PM »
ethanol/water screams SN1 to me.
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