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Topic: Friedel-Crafts Acylation of Benzene  (Read 3342 times)

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Offline zeoblade

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Friedel-Crafts Acylation of Benzene
« on: May 20, 2011, 10:52:05 PM »
After you add the acylium ion and the carbonyl oxygen complexes AlCl3, water is added to release the product.

Is this the same reason with NaBH4 reduction of ketones?

Offline Schrödinger

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Re: Friedel-Crafts Acylation of Benzene
« Reply #1 on: May 21, 2011, 02:33:35 AM »
http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch15/ch15-2-6.html

The above link is for LiAlH4, but I think the mechanism for NaBH4 is similar to this.
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Offline zeoblade

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Re: Friedel-Crafts Acylation of Benzene
« Reply #2 on: May 21, 2011, 02:39:24 AM »
Thank you,

So does this mean you also think adding water to release the ketone from AlCl3 is the same as adding water when reducing a ketone with NaBH4?

I'm just not very sure about the mechanism of how the water releases the ketone produced from Friedel-Crafts acylation of benzene

Offline BluePill

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Re: Friedel-Crafts Acylation of Benzene
« Reply #3 on: June 03, 2011, 07:32:51 AM »
I am not sure if you really need water in Friedel-Crafts acylation. I thought (by my reckoning) that AlCl3 requires anhydrous conditions.

If I remember my inorganic chemistry right, AlCl3 is ionic. Therefore, it would a complex in the presence of water (which I think is undesirable considering that you need AlCl4- in the end).

Offline Schrödinger

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Re: Friedel-Crafts Acylation of Benzene
« Reply #4 on: June 06, 2011, 04:18:27 AM »
Yes. AlCl3 requires anhydrous conditions.
But I don't think AlCl3 is ionic, although it's aqueous solution is.
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