How is this correct? (Organic; Stereochemistry)

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SUMMARY

The discussion centers on the correct assignment of (R) and (S) configurations for the compounds 1-bromo-1-chloroethane and 1-bromo-1-methoxypropane. Participants analyze the priority of substituents based on Cahn-Ingold-Prelog rules, concluding that the (R)-enantiomer is incorrectly identified as (S) for both compounds. The confusion arises from the positioning of the lowest priority group, hydrogen, and its orientation in Newman projections. Ultimately, the consensus is that both compounds are indeed (S)-enantiomers.

PREREQUISITES
  • Cahn-Ingold-Prelog priority rules
  • Newman projections for stereochemical representation
  • Understanding of enantiomers and chirality
  • Basic organic chemistry knowledge, particularly regarding substituent effects
NEXT STEPS
  • Study the Cahn-Ingold-Prelog rules in detail
  • Practice drawing Newman projections for various organic compounds
  • Explore stereochemical nomenclature for complex molecules
  • Review examples of enantiomeric pairs and their properties
USEFUL FOR

Organic chemistry students, educators, and professionals involved in stereochemistry and molecular modeling will benefit from this discussion.

Marconis
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Draw Newman projections depicting the (R)-enantiomer of each of the following:
a) 1-bromo-1-chloroethane
b) 1-bromo-1-methoxypropane

Picture3.png


Now, I am SURE that I am mistaken, but isn't that an (S)-enantiomer for each? Assigning priorities:

For a) Br > Cl > CH3 > H...right? So, wouldn't the (R)-enantiomer have the Br and Cl switched? With Br on the top, you have priority 1 at the top, 2 at the bottom right, 3 in the middle, and 4 on the bottom left. Isn't that a clockwise direction, with 4th priority facing away from us? Or, is that H facing towards us...help!

Same goes for b, I switched the OCH3 and the Br...Something is really messing me up that is causing me to do this. Thank you in advance!
 
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Marconis said:
with 4th priority facing away from us? Or, is that H facing towards us...help!
When you assign R and S, you let the 4th priority group face away from you. I've been picturing it so that the central atom, presumably carbon, is in the middle and the 4th priority atom, presumably hydrogen, is eclipsed by the central carbon and points directly away from you.

anyway, I'm pretty sure a is S and b is also S too. maybe the key is wrong or we're both making the same mistake?
 
Yeah, I really have no idea. A lot of answers have been wrong in the past, but for this chapter, it really grinds my gears not to have faith in the answer key.
 

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