December 23, 2024, 10:01:18 PM
Forum Rules: Read This Before Posting


Topic: Absolute configuration of alpha pinene  (Read 3959 times)

0 Members and 1 Guest are viewing this topic.

Offline AlbertoA

  • Regular Member
  • ***
  • Posts: 32
  • Mole Snacks: +0/-1
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline AlbertoA

  • Regular Member
  • ***
  • Posts: 32
  • Mole Snacks: +0/-1
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.

Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Sponsored Links