September 23, 2019, 01:13:17 AM
Forum Rules: Read This Before Posting


Topic: Stereochemistry  (Read 5352 times)

0 Members and 1 Guest are viewing this topic.

Offline specialk08

  • Regular Member
  • ***
  • Posts: 46
  • Mole Snacks: +0/-0
Stereochemistry
« on: October 17, 2011, 06:16:09 PM »
So I have a question, I need confirmation if it is correct or not...

Which of the two chair conformations of trans-1,2-dichlorocyclohexane is the lowest energy conformer?

So it would be the chair conformer which has both chloros in the equitorial position, because of steric hindrance.. correct?

And another question....we didn't cover this in class yet so I'm unsure on how to proceed.

Compound D with molecular formula C6H12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation D is converted to E (C6H12) and E is optically inactive. Propose structures for D and E.

Thanks in advance for the assistance!

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +467/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Stereochemistry
« Reply #1 on: October 17, 2011, 07:00:32 PM »
Which of the two chair conformations of trans-1,2-dichlorocyclohexane is the lowest energy conformer?

So it would be the chair conformer which has both chloros in the equitorial position, because of steric hindrance.. correct?

Yes. The key phrase is 1,3-diaxial strain.

Quote
Compound D with molecular formula C6H12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation D is converted to E (C6H12) and E is optically inactive. Propose structures for D and E.

Hints: Compound D is a racemic mixutre. The source of asymmetry must be an alkene.
« Last Edit: October 18, 2011, 03:09:24 AM by Dan »
My research: Google Scholar and Researchgate

Offline specialk08

  • Regular Member
  • ***
  • Posts: 46
  • Mole Snacks: +0/-0
Re: Stereochemistry
« Reply #2 on: October 17, 2011, 08:04:19 PM »
Which of the two chair conformations of trans-1,2-dichlorocyclohexane is the lowest energy conformer?

So it would be the chair conformer which has both chloros in the equitorial position, because of steric hindrance.. correct?

Yes. The key phrase is 1,3-diaxial strain.

Quote
Compound D with molecular formula C6H12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation D is converted to E (C6H12) and E is optically inactive. Propose structures for D and E.
[\quote]

Hints: Compound D is a racemic mixutre. The source of asymmetry must be an alkene.


Hm! Okay I think that will help along with my textbook.. thanks a lot :)

Offline specialk08

  • Regular Member
  • ***
  • Posts: 46
  • Mole Snacks: +0/-0
Re: Stereochemistry
« Reply #3 on: October 18, 2011, 03:43:48 PM »
ANother question that I don't feel I need a new thread for....

Adamantane (

How many 6 membered rings are there in this structure?

I determined that there were 4....I think?

Also, how many are in the chair conformation...for some reason I also got 4 for this but I'm not sure if it is right because there is also a space to fill in how many are in the boat conformation :/

Offline fledarmus

  • Chemist
  • Sr. Member
  • *
  • Posts: 1676
  • Mole Snacks: +203/-28
Re: Stereochemistry
« Reply #4 on: October 18, 2011, 04:31:45 PM »
That looks right to me  :D

Offline specialk08

  • Regular Member
  • ***
  • Posts: 46
  • Mole Snacks: +0/-0
Re: Stereochemistry
« Reply #5 on: October 18, 2011, 04:34:41 PM »
so it makes sense that there are 4 chair conformations and 0 boat conformations? i thought maybe it did because the chair conformation is so much more common but then i was second guessing myself

Sponsored Links