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Addition Reactiom


koolman

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why the product I formed is not formed and how the correct product is formed.

My organic chemistry is very rusty but what I am sure about is that Ag+ will not form an organometallic covalent bond here. So that is wrong, almost for sure.  Br- is a potential leaving group so if you have an SN1 process it might leave, creating a carbonium ion CH2⁺-CH=C [etc] which would be a resonance hybrid with CH2=CH-C⁺ [etc]. So if that were the mechanism you might well get some F attaching to C3 and well as C1. I suspect though that your teacher is telling you this is not SN1 but SN2, i.e.  the fluoride pushes the bromide off. Does that seem like a plausible explanation? 

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