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Topic: Racemic mixture - enantiomeric forms  (Read 5827 times)

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Offline mass

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Racemic mixture - enantiomeric forms
« on: May 14, 2008, 09:04:39 AM »
How can a racemic micture of two enantiomeric alcohols be resolved into 2 steroisomers.

At first, I thoughtt react with a diastereoismer and then you get two isomers with different physical properties which can been seperated. However, I have been told by the lecturer that, you have react with another pure enantiomer.

Offline sjb

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Re: Racemic mixture - enantiomeric forms
« Reply #1 on: May 14, 2008, 09:58:52 AM »
You essentially have the right idea.

If you have, for instance (R) and (S) mandelic acid, you can react the mixture with, for instance, enantiomerically pure (R)-alpha-methylbenzylamine to form diastereomeric salts (or further, amides) that you may be able to recrystallise or elute separately. If you had a mixture of (R) and (S)alpha-methylbenzylamines you would form the enantiomeric pair of diastereomers (R),(R) and (S),(S), which are identical in a achiral environment, and the (R),(S) and (S),(R) forms which too are identical, but diastereomeric to the first pair.

Remember, enantiomers react identically, unless in an chiral enviroment.

Offline movies

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Re: Racemic mixture - enantiomeric forms
« Reply #2 on: May 14, 2008, 01:17:06 PM »
Great answer!!

Offline mass

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Re: Racemic mixture - enantiomeric forms
« Reply #3 on: May 23, 2008, 08:16:55 AM »
Would you use the same process to resolve two enantiomeric alcohols or is that a different method? someone mentioned esterification but I am not so sure about that.

Offline sjb

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Re: Racemic mixture - enantiomeric forms
« Reply #4 on: May 25, 2008, 02:49:52 PM »
Pretty much the same idea, if you have a racemic sample of alcohol, do something to it so you get diastereomers, then get enantio-enriched samples of alcohol back afterwards.
 

Offline mass

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Re: Racemic mixture - enantiomeric forms
« Reply #5 on: May 25, 2008, 03:09:53 PM »
after converting them to diasteremoismers, do you use crystallisation to seperate them or is there a  different method.

Offline sjb

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Re: Racemic mixture - enantiomeric forms
« Reply #6 on: May 26, 2008, 04:23:40 AM »
Recrystallisation, columns, distillation, ... anything in principle goes.

S

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