Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: myelver10 on November 18, 2004, 06:10:34 PM

Title: sulfonates in nucleophilic substitutions
Post by: myelver10 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

Title: Re:sulfonates in nucleophilic substitutions
Post by: dexangeles 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

Title: Re:sulfonates in nucleophilic substitutions
Post by: Donaldson Tan on November 21, 2004, 09:47:08 AM

Isn't the C-I bond very weak?

Title: Re:sulfonates in nucleophilic substitutions
Post by: Mitch on November 21, 2004, 04:07:22 PM

ethanol/water screams SN1 to me.