I stumbled upon an interesting organic chemistry problem:

Reaction of AlCl3 with alkenes

Previously I thought $\ce{AlCl3}$ would only be used with benzene in acylation and alkylation, but apparently it can also be used in reactions with alkenes. Because of this, I am wondering what the product of the reaction above will be. My first thought was that there is an addition of $\ce{HCl}$ to the alkene and then the $\ce{AlCl3}$ would react in some way, though this is very likely incorrect. This left me wondering what the role of $\ce{AlCl3}$ is in this particular reaction and whether the $\ce{HCl}$ is just a catalyst.

  • 2
    $\begingroup$ This has an answer for using $\ce{AlCl3/HCl}$ in alkylation of benzene using alkenes. I believe this method is a shortcut without using alkyl chloride as an alkylating reagent. Thus, I think alkyl chloride might be the product (or alkyl may be polymerized). $\endgroup$ Commented Apr 10, 2020 at 2:12
  • $\begingroup$ I was doing this problem too and I thought that since AlCl3 is a Lewis acid, it should coordinate with one of the fluorines. This makes it a good leaving group so the chloride attacks beta to the carbon with fluorines. Then addition of HCloccurs on the resulting alkene, so that Cl is added to the carbon with the fluorine in regular markovnikov fashion. $\endgroup$ Commented May 14, 2020 at 2:26
  • $\begingroup$ are you doing IChO from the US or another country? $\endgroup$ Commented May 14, 2020 at 2:28


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