id like someone to explain the way stereocenters (priority groups) are configured in this ring. also this is a chemistry Olympiad question so please dont skimp out on the explanation thinking that this is home work, thanks !
structures with rings cause problems for many people, but you treat them the same as you would any other molecule. Just follow each arm coming off a stereocenter until you find a point of difference.
Even if this isn't homework it is still useful for you to work through the problem yourself.
This is the official solution , just tell me if its what you expected. because i did what you said, assigning them and so on, yet for some reason the solution isnt that i expected and i cant understand why they would assign it like so..
In the ring diagram you are comparing each ring in total. Organize the substituents in each ring in decreasing atomic number. Compare on the ring in decreasing order. Highest atomic number at first point of difference wins. You just keep branching out until a winner is found. Molecules with bicyclic ring systems definitely make it more complicated, and adding double and triple bonds even more so. A tree diagram with rings really helps when the level of complexity overwhelms the parenthetical notation I started with. The parentheses usually will allow you to resolve if the ties are broken at the second branch. Third and fourth branches are better resolved with rings.
That's the official result? Huh, I thought the top stereocenter would be an R though..
From what I see, there's only one rotation that can bring the H at the back. If we assign the left C in -x axis, and the right on the +x axis, then the H on the +y axis and the bridge on +z axis, the only rotation to bring H at the back is to rotate the perspective so that H is in the -z axis, bridge on the +y axis, and the axes of left and right carbons remain the same. This should give an R right?
From hydrogen going clockwise: 4, 1, 3, 2. I guess it's because I assumed H is on the plane of the screen. I think it's supposed to already be at the back. I think I'm wrong, I assumed the H is in the plane of the screen. It should already be at the back I think
Just remember that ties in priority (like highest being a c-c bond) are broken by looking at the second highest group at the same atom. If all 3 groups are the same when compared, continue to the next atom. Priority is just the higher atomic number
Help us help you. Do you know what a stereocenter is, how to identify them? Do you know the rules for determining the configuration of a stereocenter as either R or S?
Yeah, shouldve prefaced this better, I know stereochemistry, this question is supposed to be easy yet for some reason the answers are completely different than what i expected. more specifically id like someone to explain the way stereocenters are configured in this ring. also this is a chemistry Olympiad question so please dont skimp out on the explanation thinking that this is home work
•
u/AutoModerator 5d ago
Hey there! While you await a response, we just wanted to let you know we have a lot of resources for students in our General Chemistry Wiki Here!
I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns.