Reaction to the product stereochemistry

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SUMMARY

The discussion focuses on determining the stereochemistry of a reaction product involving two stereocenters, specifically identifying configurations as R or S. The reaction is identified as an E1 elimination due to the use of potassium t-butoxide, a strong base, in a polar solvent (t-butanol). The presence of an allylic bromine suggests that the reaction will favor a carbocation mechanism, as the C-Br bond can break to form a resonance-stabilized carbocation. The final stereochemical configurations of the product can be one of R,R; R,S; S,R; or S,S.

PREREQUISITES
  • Understanding of stereochemistry, including R and S configurations.
  • Knowledge of elimination reactions, specifically E1 and E2 mechanisms.
  • Familiarity with the role of solvents in reaction mechanisms, particularly polar solvents.
  • Basic concepts of carbocation stability and resonance.
NEXT STEPS
  • Study the mechanisms of E1 and E2 eliminations in organic chemistry.
  • Learn about stereochemical representation using wedge and dash notation.
  • Explore the effects of solvent polarity on reaction mechanisms.
  • Investigate the stability of carbocations and the factors influencing their formation.
USEFUL FOR

Chemistry students, organic chemists, and anyone studying reaction mechanisms and stereochemistry in organic reactions.

ahazen
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I need help writing the reaction to the product.
I know the wedge and dash are R and S.

I am stuck on what to do...please help me

Thank you
 
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I am stuck on what you are stuck on. Any image, details?
 


oops, sorry about that.
Here is the structure image
 

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You have two stereocenters there. Arrange them so that the hydrogens are dashed. Determine the priority order. Go from highest priority to lowest. Clockwise is R.

Your answer will be one of R,R; R,S; S,R; S,S.
 


thank you so much:)
 


Are you trying to determine the product of this reaction? It's going to be an E1 elimination. I'll explain how I figured that out:

-Potassium t-butoxide is a strong base and a weak nucleophile, so nucleophilic substitution will be unlikely (and that is a competitive reaction with eliminations). This leaves you with two options: E1 or E2 elimination.
-E2 elimination is unlikely in a polar solvent (t-butanol).
-The substrate molecule has an allylic bromine. If the C-Br bond were to spontaneously break, the carbocation formed would have resonance stabilization. As such, a mechanism involving a carbocation is likely, especially considering that the solvent is polar and can stabilize the carbocation even more.
 


Thank you:)
 

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