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Reactions involving magnesium
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Topic: Reactions involving magnesium (Read 4570 times)
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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?
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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)
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kanonsviel
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Re: Reactions involving magnesium
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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?
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kingsfan
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Re: Reactions involving magnesium
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Reply #3 on:
November 07, 2010, 12:00:50 AM »
correct
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jake.n
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Re: Reactions involving magnesium
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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.
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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
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karvon
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Re: Reactions involving magnesium
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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?
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jake.n
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Re: Reactions involving magnesium
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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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