Substitution reaction and configuration

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SUMMARY

The discussion centers on the substitution reaction of (2S,3S)-2-chloro-3-methylpentane with a high concentration of CH3O-. The primary focus is on the product formation, where the -Cl group is replaced by -OCH3. The participant concludes that the configuration changes from 2S to 2R, but faces confusion regarding the stereochemistry of the product, questioning whether it should be (2R,3R) or (2R,3S). The possibility of an E2 elimination reaction is also raised, indicating the complexity of the reaction pathway.

PREREQUISITES
  • Understanding of stereochemistry and chirality in organic compounds
  • Knowledge of substitution reactions, specifically SN2 and E2 mechanisms
  • Familiarity with the concept of asymmetric centers in organic molecules
  • Proficiency in drawing and interpreting molecular structures
NEXT STEPS
  • Study the mechanisms of SN2 and E2 reactions in detail
  • Learn about stereochemical configurations and how to determine them
  • Explore the effects of sterics and electronics on substitution reactions
  • Practice drawing and analyzing products of substitution reactions with asymmetric centers
USEFUL FOR

Chemistry students, organic chemists, and educators looking to deepen their understanding of substitution reactions and stereochemistry in organic compounds.

Thecoolone
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Homework Statement



(2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O- ---> ?


The Attempt at a Solution



I need to find the product and usually my method is to knock off the -Cl replacing it by
-OCH3 and when drawing the compound I just make an mirror image. In (2S,3S)-2-chloro-3-methylpentane there are two asymmetric centers and for the product with Cl replaced with OCH3 I assume that it changes configuration so that it becomes 2R instead of 2S. My problem is now, that I cannot draw the product without getting (2R,3R).
Is this correct? I assume that it should be 2R,3S because I do not knock off any atom or molecule from the second asymmetric center.
 
Physics news on Phys.org
It is a secondary halide adjacent a tertiary carbon center. You sure you're going to get Sn2 product? How about E2?
 

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