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Topic: Chair interconversion stereoisomers  (Read 3579 times)

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Offline cabaal

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Chair interconversion stereoisomers
« on: October 29, 2010, 06:38:45 PM »
Is there a quick trick for finding out if two chair conformations of cyclohexane are enantiomers or diastereomers? Building the models out doesn't really work because my model set is too rigid to do a chair flip and I cannot see the structure in my head.

Offline MissPhosgene

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Re: Chair interconversion stereoisomers
« Reply #1 on: October 29, 2010, 06:47:12 PM »
Try writing the ring-flips on paper as flat structures with bold and dashed lines as bonds between carbon atoms.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline cabaal

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Re: Chair interconversion stereoisomers
« Reply #2 on: October 29, 2010, 06:50:20 PM »
Try writing the ring-flips on paper as flat structures with bold and dashed lines as bonds between carbon atoms.

It's definitely much, much easier that way. Thank you.

Offline MissPhosgene

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Re: Chair interconversion stereoisomers
« Reply #3 on: October 29, 2010, 09:19:36 PM »
Glad it helped.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline movies

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Re: Chair interconversion stereoisomers
« Reply #4 on: October 30, 2010, 09:14:21 AM »
The other trick is to just rotate each substituent one position around the ring.

Offline svalbard

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Re: Chair interconversion stereoisomers
« Reply #5 on: October 31, 2010, 05:50:08 PM »
I usually just find how many steriocenters there are, then calculate the number of isomers i.e. 2^n
Then draw them as a "flat" ring with cis/trans.

for me it's easier to see it as cis/trans on the ring when determining enantomeric isomers.


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