Questions Chiral centers,Markonikov's rule

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SUMMARY

The discussion centers on the identification of chiral centers in organic compounds, specifically 3- and 4-vinylcyclohexanethiol. Participants confirm that 3-vinylcyclohexanethiol contains two chiral centers, while 4-vinylcyclohexanethiol has only one. The importance of understanding Markovnikov's rule and the anti-addition of Br2 to double bonds is emphasized. Additionally, the amine is clarified as not being a chiral center and not reactive with chiral alcohols.

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  • Understanding of chiral centers in organic chemistry
  • Familiarity with Markovnikov's rule
  • Knowledge of anti-addition reactions, specifically involving Br2
  • Experience with molecular modeling techniques
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I put all of my questions/solutions in the attached file...could someone please check over them before 7:00 am to see if I have them correct? Thanks in advance!
 

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Question 1:
part c) H2S is a product, not a reactant.
part d) You're missing a chiral center. The 4-position Carbon is chiral for the elimination products. It's not quite symmetrical.

bonus looks correct!
 
Bonus is wrong. There are 2 chiral centers and neither is near enough to the amine to cause racemization. The amine is not a chiral center.

3- and 4-vinylcyclohexanethiol each have 2 chiral centers.

e) is wrong since Br2 adds anti to double bonds, not randomly. You need to make models to see it maybe.
 
Last edited:
chemisttree said:
Bonus is wrong. There are 2 chiral centers and neither is near enough to the amine to cause racemization. The amine is not a chiral center.

I hate it when I rush through these questions! I'm wrong, of course. You were correct in your answer that there is only one chiral center. That said, the amine is certainly not a chiral center and is not reactive with the chiral alcohol.

3- and 4-vinylcyclohexanethiol each have 2 chiral centers.

Arrrrgggghhhh! I did it again here! There are 2 chiral centers on the 3-vinyl compounds and only 1 for the 4-vinyl compounds.

e) is wrong since Br2 adds anti to double bonds, not randomly. You need to make models to see it maybe.

Got that one right.
 

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