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Topic: reaction of carbonyl compounds with LiAlH4 to produce alcohols  (Read 6504 times)

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Offline Seks

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(1) LiAlH4 in Et2O
(2) HCl in H2O

My instructor said not to use H2SO4 in H2O for step (2) as it's not recommended.  She didn't say why.  So why can't I use H2SO4 in H2O?  My initial assumption was that I can use any aqueous acidic solution?  ???

Offline agrobert

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Re: reaction of carbonyl compounds with LiAlH4 to produce alcohols
« Reply #1 on: March 04, 2008, 07:18:43 PM »
What is the purpose of the acid?

Which acid is stronger?
In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline Seks

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Re: reaction of carbonyl compounds with LiAlH4 to produce alcohols
« Reply #2 on: March 04, 2008, 07:33:03 PM »
What is the purpose of the acid?

Which acid is stronger?

Neutralize the solution.  HCl is stronger.

 ???

Offline agrobert

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Re: reaction of carbonyl compounds with LiAlH4 to produce alcohols
« Reply #3 on: March 04, 2008, 07:53:56 PM »
The acidic work-up also protonates what?  You need a strong acid to neutralize a strong _____ efficiently.  What is your base?
In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline sjb

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Re: reaction of carbonyl compounds with LiAlH4 to produce alcohols
« Reply #4 on: March 05, 2008, 11:43:31 AM »
It might be that H2SO4 is too viscous, so you won't be able to stir effectively and may not quench all the LiAlH4 well.

I'm surprised you're using mineral acid to work LiAlH4 reductions up though, what sort of scale are you talking? Typically I thought you used things like the Fieser work-up procedure - http://www.chemicalforums.com/index.php?topic=9767.msg46338, I've certainly done this on 30-40g of LAH before now...

Is this just a "chemistry en papier" question?

S

Offline sjb

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Re: reaction of carbonyl compounds with LiAlH4 to produce alcohols
« Reply #5 on: March 06, 2008, 10:28:36 AM »
It might be that H2SO4 is too viscous, so you won't be able to stir effectively and may not quench all the LiAlH4 well.

ERm, ranmbling again, forget that. Does H2SO4 (or perhaps more specifically, the sulfate and bisulfate anions) do anything else to alcohols

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