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Organic Chemistry Forum / Re: Cahn-Ingold-Prelog ACS Question on YouTube
« Last post by benz0icacid on May 18, 2024, 03:44:04 PM »
I agree. Also, it doesn't make sense for it to be 2R, 3S and it's cis. It would be 2R, 3R, if I'm not mistaken.
Thanks!
edit: exactly, @Hunter2. Thank you!
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Organic Chemistry Forum / Re: Cahn-Ingold-Prelog ACS Question on YouTube
« Last post by Hunter2 on May 18, 2024, 03:43:44 PM »
It should be the cis - 4-bromo-2R,3R epoxy- butan-1-ol.
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Organic Chemistry Forum / Re: Cahn-Ingold-Prelog ACS Question on YouTube
« Last post by Babcock_Hall on May 18, 2024, 03:07:26 PM »
The video looks incorrect to me.
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Organic Chemistry Forum / [Solved] Cahn-Ingold-Prelog ACS Question on YouTube
« Last post by benz0icacid on May 18, 2024, 02:12:36 PM »
Hello!
I'm watching an ACS Ochem 2 Exam Review: https://www.youtube.com/watch?v=OQctLH-psYc&list=PL3A1cf8LCsnlSRO3HEygntDa4cd9tQh2U&index=1

At timestamp 4:30, we are assigning R and S configuration for the epoxide's carbon #3. We are comparing the carbon with O, C, H, and the carbon connected to Br, H, H. The carbon connected to OCH is given 2nd priority, and the carbon with BHH is given 3rd priority. Why is that? I thought since Br has the higher mass, it would have 2nd priority?

I also found a similar question on R/MCAT: https://www.reddit.com/r/Mcat/comments/91mzf1/br_or_oh_higher_priority/

I would appreciate the clarification. Thank you for your time and patience!
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Organic Chemistry Forum for Graduate Students and Professionals / Re: Sulfamidophosphonate synthesis via n-butyllithium: ratio of starting materials
« Last post by rolnor on May 17, 2024, 05:37:15 PM »
Quote from: Babcock_Hall on May 17, 2024, 09:42:36 AM
https://pubs.acs.org/doi/10.1021/acs.jmedchem.8b01523 
Granberg KL, J. Med Chem. 2019, 62, 3, 1385-1406. 

One thing that attracted me to this method is that the ratio of the methyl sulfonamide to base to the chlorophosphate is 1:2:1; in other words, there is not the approximate twofold of excess of the methyl sulfonamide over the phosphorylating agent that I found in most other protocols.  As to what is different, my speculation is that the steric bulk of this base prevents it from removing a proton from the product, which is more acidic than the starting material.

Or maybe the product becomes a TMS enol? I know that ethyl acetate is best lithiated by LiHMDS it gives better yields, better than LDA. Its interesting. I dont know if steric bulk stops deprotonation, maybe it does
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