Stereochemistry - R S Configuration & Fischer Projections
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- Опубліковано 4 жов 2024
- This video provides an overview of the stereochemistry of organic compounds and defines what exactly a chiral carbon center is. This video also shows you how to assign R and S configuration to a chirality center whenever the hydrogen (4th group) atom is in the front, back, or neither. It also discusses nomenclature - how to name organic compounds using R and S absolute configuration. It provides a lot of examples and practice problems.
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Thanks Man! Hope to get a like :)
In minute 17:00 shouldn't there be 9 chiral centers and not just 8. I am referring to the carbon under the second carbon that you numbered. Isn't that also a chiral center since it is attached to 4 different groups?
@@Curiousviewer23 I thought the same too but I just goggled for the structure of cholesterol and he has the wrong structure....the particular c you speak of own the double bond too that was put away
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TY, I appreciate all your hard work. I watch many of your videos and they have helped a lot! ***Possible CORRECTION? looks like the cholesterol molecule in your video has the double bond in the wrong place. *** I kept going over and over this and could not understand why Carbon-5 (the one due south of the methyl group) was not a chiral center? As the figure is drawn, it should be...which would make 9 stereocenters, not 8. But when I looked up cholesterol, the double bond is actually between C-5 and C-6 not as you've shown it. Just in case anyone else got stuck on this problem.
Same for me
Thanks for this comment. I've been sitting here the past few minutes trying to figure out why there would only be 8 given the drawing in the video. After looking up what cholesterol should look like, it makes sense.
I have struggled for this question as well until I found out your comment.
It seems that there are 2^9=512 different stereoisomers in cholesterol.
thanks can't believe I realized it
I saw that too, the double bond is in a wrong position. All the same thank you 🙏
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Another incredible video; thanks so much for posting! If the hydrogen (or lowest priority group) isn't where I want it to be, sometimes I just exchange two groups to make that happen, and remember that that inverts the stereochemistry (R -> S or vice versa).
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Same
the double bond in the cholesterol is incorrect. it needs to be moved one bond to the left. I kept thinking there were 9 chiral centers until I googled it. Keep up the great work!!
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17:08, isn't there another chiral center below carbon #2, since first bond goes to a sp3 C, second to sp3 CH2, and third to a sp2 CH and a hydrogen?
yess there are 9 not 8 chiral Cs
Brilliant you are correct.. Wanted to ask too
Yes, he drew the molecule with the double bond in the wrong place. Cholesterol has 2^8 isomers but the drawn molecule has 2^9.
He made a small error and drew the double bond in the wrong place. So, you're right that the molecule shown has 9 stereocenters! In reality, cholesterol only has 8. You can confirm this by googling the molecule. xx
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The position of the C=C in cholesterol is wrong, according to your drawn diagram, there should be 9 chiral centers, but for cholesterol, there is only 8 because of the positioning of the C=C. But other than that, I loved the video and it helped me a lot in understanding stereochemistry.
For Q3, the one assigning chiral centers for Cholesterol, would there not be a chiral carbon just below the 2nd chiral carbon? It is attached to a sp2 hybridized carbon, the carbon with a methyl group, and a ch2 carbon that eventually leads to an alcohol
yes, it is chiral so there are 9 chiral centers
Yes, he drew the double bond incorrectly, the two cicle hexanes are supposed to be "fused" via a double bond between the carbon under chiral carbon 2 and the carbon to it's right, so in the cholesterol molecule there are only 8 chiral centers, but the molecule shown in the video has 9 chiral centers.
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When identifying the chiral centers on cholesterol, I think you accidently missed one and it would be 9 instead of 8. Isn't there a chiral center on the carbon below the one you indentified as 2?
You are right! Based off of his structure, there are 9 chiral centers. However, the double bond in his cholesterol drawing is in the incorrect position; it should be moved one spot to the left. After that change, there will only be 8 chiral centers
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at 17:30 there is an another chiral carbon on the left of the double bond
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27:19 I got (2R,3S)-3-bromo-2-chloro-1-butanol for problem 5
hmmm I got (2S,3R)-3-bromo-2-chloro-1-butanol
I converted the newman projection to a stick model first. The parts on the left go on dashes and the parts on the right go on wedges.
On carbon 2 Cl is on a dash and H is on a wedge. Cl is 1, the carbon bonded to Br is 2, the carbon bonded to OH is 3, and H is 4. Numbers increased going CCW so that would be S, but because H is wedged it is R.
On carbon 3 Br is on a wedge and H is on a dash. Br is 1, the carbon bonded to Cl is 2, the CH3 is 3 and H is 4. Numbers increased CCW so that would be S.
I still get (2R,3S)-3-bromo-2-chloro-1-butanol.
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In problem 3, why is the tertiary carbon closest to the double bond not considered a chiral center? I am talking about the bottom right carbon on the farthest benzene to the left of the cholesterol.
I noticed that too, I think he just over looked that one
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I've got a question regarding the Hydrogen Atoms in the Cholesterol Molecule. Did you follow any rules when placing the Hydrogens in between the Carbon structure regarding their position behind or in front of the planes? Or is their position arbitrary? Thank you so much for this great tutorial. It really helps!
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