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Topic: Friedel Crafts alkylation  (Read 2168 times)

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Offline kirushanth

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Friedel Crafts alkylation
« on: August 08, 2012, 02:45:28 AM »
When we do a Friedel Crafts Alkylation, using AlX3 also includes rearrangement. To prevent that, we do an acylation and then a reduction of the ketone. My friend told me usage of FeX3 doesn't involve rearrangement in alkylation itself. Is he right?

Offline Schrödinger

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Re: Friedel Crafts alkylation
« Reply #1 on: August 08, 2012, 08:17:53 AM »
The concept is the same in both the cases. Both being Lewis acids, will abstract that halogen and transform  the alkyl halide into a carbocation. Hence, rearrangement is possible in both the cases, whether AlCl33or FeCl3. I don't think Fe is special in any way, although I might be wrong.  Maybe someone who has had practical experience with this in the lab can comment.
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Offline kirushanth

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Re: Friedel Crafts alkylation
« Reply #2 on: August 08, 2012, 12:02:56 PM »
I told him exactly that. He said:
Consider the case of chlorine.When we use FeCl3, it pulls Cl- weaker than AlCl3 and so, as a result, Cl is partially attached to the alkyl group still clinging with it, ever after it was taken by FeCl3. The carbocation is not fully formed and as a result, this does not allow rearrangement to take place.
I found this rather surprising and decided to ask the forum experts.

Offline Schrödinger

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Re: Friedel Crafts alkylation
« Reply #3 on: August 08, 2012, 01:09:39 PM »
Unless you have experimental evidence, these sort of questions tend to be open-ended. In organic chemistry, one can always argue saying that some factor x is more important than factor y, but unless you have experimental evidence, I guess it's difficult to really say for sure.
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