Reaction to the product stereochemistry

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Discussion Overview

The discussion revolves around determining the stereochemistry of a reaction product involving stereocenters and the mechanism of an E1 elimination reaction. Participants seek clarification on how to represent stereochemistry and the implications of reaction conditions on the mechanism.

Discussion Character

  • Technical explanation
  • Conceptual clarification
  • Homework-related
  • Debate/contested

Main Points Raised

  • One participant seeks assistance with writing the reaction product and understanding the stereochemistry represented by wedge and dash notation.
  • Another participant requests additional details or images to better understand the initial query.
  • A participant identifies that there are two stereocenters and suggests arranging them with hydrogens as dashed, determining priority order for stereochemistry notation.
  • A different participant proposes that the reaction is likely an E1 elimination due to the nature of the base and solvent, explaining the reasoning behind this conclusion.
  • Participants express gratitude for the assistance provided throughout the discussion.

Areas of Agreement / Disagreement

There is no consensus on the specific stereochemical outcome of the reaction, as participants are still exploring the details of the stereocenters and the elimination mechanism. Multiple views on the reaction mechanism exist, particularly regarding E1 versus E2 elimination.

Contextual Notes

Participants have not fully resolved the assumptions regarding the stereochemistry and the specific reaction conditions that influence the mechanism. The discussion includes varying interpretations of the reaction pathway based on the substrate and solvent used.

Who May Find This Useful

This discussion may be useful for students or individuals interested in organic chemistry, particularly those studying stereochemistry and reaction mechanisms.

ahazen
Messages
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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
 

Attachments

  • Stereochemistry.jpg
    Stereochemistry.jpg
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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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