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A vinylic halide will not do the SN1 reaction since a carbocation would be highly unstable especially if no R groups are attached. The vinylic halide would not do an SN1 reaction mainly because rehybridization would necessitate that an sp transition state would form.....this is VERY High energy, and reduces the rate. Also, a backside attack would not be feasible. Examine a model to confirm this. An allylic halide can form a Wickedly fast SN1...due to a very stable carbocation. If the halide is primary, a backside attack can occur as well....and an SN2 reaction occurs. A polar solvent would favor the Sn1 process. Hope this helps. Dr. Jim Romano CEO Romano Scientific CEO Orgoman.com New York

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Q: Why vinylic chloride is least reactive towards SN reactions while allylic chlorides are highly reactive?
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