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Grignard reaction on ester - stereochemistry
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Topic: Grignard reaction on ester - stereochemistry (Read 7424 times)
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2moles
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Grignard reaction on ester - stereochemistry
«
on:
May 26, 2009, 05:47:21 AM »
Hi!
I have a question here... I have an ester reacting with 2 moles of CH3MgBr. I know my product is a tertiar alcohol, but how is the stereochemistry? Is it possible to know whether it is the R or S configuration? Or doesn't this matter since the two methylgroups are the same?
A bit confused..
Thanks if you answer
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Arctic-Nation
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Re: Grignard reaction on ester - stereochemistry
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May 26, 2009, 08:46:03 AM »
It does indeed not matter. You can only have a stereocenter with four different substituents, so with your two methyl groups you'll never get enantiomers.
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Loyal
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Re: Grignard reaction on ester - stereochemistry
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May 26, 2009, 09:40:54 PM »
Remember that the Grignard reagent attacks the Ester once which removes the O-R group from the carbon and thus it leaves a Ketone which can react with a second mole of the Grignard. This means your R-MgCl attaches twice.
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Chemistry Student(Senior) at WSU
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Grignard reaction on ester - stereochemistry