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Topic: Absolute configuration of alpha pinene  (Read 3960 times)

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Offline AlbertoA

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Absolute configuration of alpha pinene
« on: September 03, 2011, 07:49:54 PM »
http://en.wikipedia.org/wiki/File:Alpha-Pinene_Isomers.svg
in the (-) alpha pinene what is the absolute configuration of the two chiral carbons?

Offline discodermolide

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Re: Absolute configuration of alpha pinene
« Reply #1 on: September 04, 2011, 12:09:06 AM »
http://en.wikipedia.org/wiki/File:Alpha-Pinene_Isomers.svg
in the (-) alpha pinene what is the absolute configuration of the two chiral carbons?

It's name is (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene. Perhaps this helps.
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Offline AlbertoA

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Re: Absolute configuration of alpha pinene
« Reply #2 on: September 04, 2011, 01:59:40 PM »
http://en.wikipedia.org/wiki/File:Alpha-Pinene_Isomers.svg
in the (-) alpha pinene what is the absolute configuration of the two chiral carbons?

It's name is (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene. Perhaps this helps.
My problem is with the priorities according to the CIP rules
with the "alyl" carbon it's obvious that is R, but the other chiral carbon?
the 1 will be C-C-C, the 2? C-H-H for both carbons, so we go to the next C, then C-H-H-C and the other C-H-C
what group will be 2?

Offline discodermolide

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Re: Absolute configuration of alpha pinene
« Reply #3 on: September 05, 2011, 01:35:38 AM »
http://en.wikipedia.org/wiki/File:Alpha-Pinene_Isomers.svg
in the (-) alpha pinene what is the absolute configuration of the two chiral carbons?

It's name is (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene. Perhaps this helps.
My problem is with the priorities according to the CIP rules
with the "alyl" carbon it's obvious that is R, but the other chiral carbon?
the 1 will be C-C-C, the 2? C-H-H for both carbons, so we go to the next C, then C-H-H-C and the other C-H-C
what group will be 2?


The allyl carbon (the bottom one as drawn) is (S) configured: The group with the lowest priority (H) must point away from you.

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