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Topic: Can someone explain why there would be no reaction here?  (Read 3226 times)

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Offline toadesque

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Can someone explain why there would be no reaction here?
« on: March 21, 2010, 06:56:24 PM »
When talking about Friedel-Crafts Akylations:

                                  AlCl3
aromatic ring + C=C-X    ---->    No Rxn

It would be this

aromatic ring bonded to C=C

why can this not happen?

Offline chuckycheeze

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Re: Can someone explain why there would be no reaction here?
« Reply #1 on: March 21, 2010, 09:56:22 PM »
When talking about Friedel-Crafts Akylations:

                                  AlCl3
aromatic ring + C=C-X    ---->    No Rxn

It would be this

aromatic ring bonded to C=C

why can this not happen?

first AlCl3 is used not in Friedel-Craft alkylation but in F-C acylation
                                                         R
second F-C acylation involved reactant X-C=O(acyl chloride)
so C=C as far as my concern shouldn't react.
I might be wrong though

Offline orgopete

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Re: Can someone explain why there would be no reaction here?
« Reply #2 on: March 21, 2010, 11:01:05 PM »
If we were to determine the acidity of substituted carbons, you would find the following order:
RC≡CH>R2C=CH2>RCH3

From this, we should think an sp carbon is more electron withdrawing than an sp2 carbon which in turn is more electron withdrawing than an sp3 carbon. In a Friedel Crafts alkylation reaction, we require the intermediate to be a carbocation. From the information we just considered, rate the stability of the following carbocations?
RC≡C+, R2C=CH+, and RCH2+

The problem is not with the Lewis acid used, but the difficulty in forming the required sp2-carbocation intermediate.
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Offline toadesque

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Re: Can someone explain why there would be no reaction here?
« Reply #3 on: March 22, 2010, 05:00:18 PM »
thanks

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