Free Radical Stability Homework: Find the Optimal Temp

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    Radical Stability
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Discussion Overview

The discussion revolves around determining the optimal temperature for the stability of free radicals, with a focus on factors influencing stability such as mesomeric effects and the classification of carbon types (primary, secondary, tertiary).

Discussion Character

  • Homework-related
  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant suggests that the answer to the homework question is option 3 (3 degrees C), based on their attempts.
  • Another participant questions whether there are other stabilizing factors involved, specifically mentioning a polar effect.
  • Some participants discuss the terminology used to describe carbon types, noting a preference for universal terms like tertiary and secondary over the numerical system used in the book.
  • A participant introduces the concept of the mesomeric effect as a stabilizing factor, suggesting it could rule out options 3 and 4.
  • There is a claim that the mesomeric effect always dominates in this context, implying its significance in determining stability.
  • Another participant advises considering resonance structures and mentions that radical stability trends are similar to carbocation stability trends.

Areas of Agreement / Disagreement

Participants express differing views on the factors affecting radical stability, particularly regarding the significance of the mesomeric effect and the classification of carbon types. The discussion remains unresolved with multiple competing perspectives.

Contextual Notes

There are limitations in the discussion regarding assumptions about the polar effect and the definitions of stability factors. The reliance on specific terminology and the implications of resonance structures are also not fully explored.

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Homework Statement

Homework Equations

The Attempt at a Solution


option 1: 1 degree C
option 2: 1 degree C
option 3: 3 degree C
option 4: 1 degree C

SO the answer should be option 3?
 
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Is that the only stabilizing factor involved here?
Any polar effect involved?
PS- always thought saying tertiary or secondary carbon was a more universal naming system
 
Suraj M said:
Is that the only stabilizing factor involved here?
Any polar effect involved?
PS- always thought saying tertiary or secondary carbon was a more universal naming system
Why would there be a polar effect? Carbon and hydrogen have very similar electronegativities.
Yeah tertiary and primary are the universal terms, somehow this book doesn't refer to them as tertiary and primary carbons but as 1 degree, 2 degree and 3 degree carbons.
 
By polar effect, I am referring to mesmeric effect in this case
 
Suraj M said:
By polar effect, I am referring to mesmeric effect in this case
If the mesomeric effect is considered, then option 3 and 4 are ruled out. But I don't understand why I can't just see which carbon is tertiary and say that's the most stable.
 
Mesmeric effect ALWAYS dominates here
 
Decide between 1 and 2 then
 
I suggest thinking about what types of resonance give the greatest stability. Also consider drawing out resonance structures. Radical stability trends closely resemble carbocation trends (tertiary > secondary > primary). Think about where aromaticity fits into this trend.
 

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