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Topic: Reactions involving magnesium  (Read 4571 times)

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Offline kanonsviel

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Reactions involving magnesium
« on: November 05, 2010, 10:56:57 PM »
What does it give by applying Mg to a ketone? I have searched many places, yet had few clues...
And, what product is gained in a reaction between a Grignard reagent and boric acid? ???

Offline jake.n

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Re: Reactions involving magnesium
« Reply #1 on: November 06, 2010, 08:20:59 PM »
For the first reaction, you're looking at a nucleophile (Grignard) and an electrophile (Boric Acid).  Which is more basic, hydroxide or your Grignard reagent?

For the second reaction, Magnesium is an "active metal" (i.e. reducing agent)

Offline kanonsviel

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Re: Reactions involving magnesium
« Reply #2 on: November 06, 2010, 10:18:18 PM »
So,the product of the first reaction should be PhB(OH)2?? ???
and the second an alcohol?
Do I get it right?

Offline kingsfan

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Re: Reactions involving magnesium
« Reply #3 on: November 07, 2010, 12:00:50 AM »
correct

Offline jake.n

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Re: Reactions involving magnesium
« Reply #4 on: November 07, 2010, 12:14:58 AM »
I think the boronic acid is right.

Upon further digging, I'm not sure the magnesium will reduce the ketone to an alcohol without an acidic proton.  This
 
http://books.google.com/books?id=w9lTxIaPCQIC&pg=PA240&lpg=PA240&dq=magnesium+benzene+reduction+of+ketones&source=bl&ots=KwfboIyzW6&sig=5367vUvgra5wI8kHHPi-fTarfVc&hl=en&ei=pyXWTNz2J8qgnge5y83kCQ&sa=X&oi=book_result&ct=result&resnum=10&ved=0CDUQ6AEwCQ#v=onepage&q&f=false

suggests that the reaction yields a dimerized, vicinal diol.

Offline kanonsviel

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Re: Reactions involving magnesium
« Reply #5 on: November 07, 2010, 12:49:06 AM »
I get it, that's an enough hint, thanks for your help :)

Offline karvon

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Re: Reactions involving magnesium
« Reply #6 on: November 09, 2010, 03:41:29 PM »
It shouldn't be that the Grignard reagent just deprotonate the boric acid and RH is produced?

Offline jake.n

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Re: Reactions involving magnesium
« Reply #7 on: November 09, 2010, 07:15:15 PM »
I don't believe boric acid is a proton donor, it's just electropositive.

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