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Topic: R and S designation of (+)-Carvone  (Read 6146 times)

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Offline p-orbs

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R and S designation of (+)-Carvone
« on: June 08, 2011, 07:34:13 AM »
I have a hard time dealing with stereochemistry and chiral molecules in general.
This time I'm dealing with the molecule Carvone. Seems I can't figure out how to upload an image here, so I'll post
a wikilink showing the compound instead: http://upload.wikimedia.org/wikipedia/commons/b/bf/Carvone.svg


How come the (+)-Carvone is given an S-designation? I think I'm troubling with the prioritizing of the substituents as
I feel like I should give priority to the doublebonded oxygen, and not the doublebonded carbon.
Could someone please be an angel and explain??  :'(

Offline AWK

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Offline discodermolide

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Re: R and S designation of (+)-Carvone
« Reply #2 on: June 08, 2011, 09:46:16 AM »
I have a hard time dealing with stereochemistry and chiral molecules in general.
This time I'm dealing with the molecule Carvone. Seems I can't figure out how to upload an image here, so I'll post
a wikilink showing the compound instead: http://upload.wikimedia.org/wikipedia/commons/b/bf/Carvone.svg


How come the (+)-Carvone is given an S-designation? I think I'm troubling with the prioritizing of the substituents as
I feel like I should give priority to the doublebonded oxygen, and not the doublebonded carbon.
Could someone please be an angel and explain??  :'(

Study the Cahn-Ingold-Prelog designation for the assignment of R & S configuration.
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Offline fledarmus

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Re: R and S designation of (+)-Carvone
« Reply #3 on: June 10, 2011, 10:43:23 AM »

I feel like I should give priority to the doublebonded oxygen, and not the doublebonded carbon.
Could someone please be an angel and explain??  :'(

Which double-bonded carbon?  ;) Remember, the Cahn-Prelog-Ingold rules require you to prioritize atom by atom through your substituents, not by total substituent size

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