Tungsten.Chromium
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Friedel-Crafts using Alkene or Alkyne Halides
Hello all,
It's been a few years since finishing my BS in chemistry and I'm looking to shake off the dust on my ochem knowledge. One of the reactions in ochem
that I always thought had more potential then it was given, was the Friedel-Crafts reaction.
In class, we spent a good deal of time going over the alkylation of benzene using alkyl halides (typically an alkyl-chloride) with lewis acids
(typically Aluminum Chloride). After reviewing my old textbook, I have a fairly familiar grasp on this reaction again.
What I'm curious of, is the different products that would form when using, say vinyl or allyl chloride? What about chloroethyne or chloropropyne?
Since water is pretty much a no-no for Friedel-Crafts, I think the different rearrangements would be more interesting than an aqueous reaction
without extra protons from an acid to aid in carbon stability
If anyone has any experience/theories of this, I'd love to hear them. In the meantime, I'll keep playing around on the whiteboard trying to come up
with my best guess.
Prosit!
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DraconicAcid
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Location: The tiniest college campus ever....
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The FC mechanism involves the formation of a carbocation. Allyl chloride should work fine, as it forms a very stable (i.e., easily-formed)
carbocation. Chloroethene or vinyl chloride do not form carbocations, and will not work.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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