Comparing Stability of Allylic Carbanions

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Discussion Overview

The discussion revolves around the stability of allylic carbanions formed from the cleavage of C-H bonds, as illustrated in a provided diagram. Participants explore the implications of resonance stabilization in different positions of the carbanions.

Discussion Character

  • Homework-related, Conceptual clarification, Debate/contested

Main Points Raised

  • Some participants suggest that cleavage of a C-H bond leads to the formation of a carbanion, with the stability influenced by the electronegativity of carbon compared to hydrogen.
  • There is mention of two allylic carbanions (a and b) being formed, with a focus on determining which is more stable due to resonance stabilization.
  • One participant notes that cleavage of position 'a' results in a vinylic carbanion, while position 'b' is associated with a more stable allylic carbanion.
  • A later reply corrects an earlier statement, indicating that positions 'b' and 'd' produce allylic carbanions, prompting a question about their relative stability.

Areas of Agreement / Disagreement

Participants express differing views on which allylic carbanion is the most stable, indicating that the discussion remains unresolved with multiple competing perspectives.

Contextual Notes

Participants have not fully clarified the assumptions regarding the stability of the carbanions or the specific definitions of resonance stabilization being applied.

gpavanb
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Homework Statement


Look at the diagram accompanying the question. Which has least C-H bond energy?


The Attempt at a Solution


On cleavage of a C-H bond, a carbanion is formed as carbon is more electronegative than hydrogen. So cleavage of (b) results in a carbanion stabilized by resonance
 

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gpavanb said:

Homework Statement


Look at the diagram accompanying the question. Which has least C-H bond energy?


The Attempt at a Solution


On cleavage of a C-H bond, a carbanion is formed as carbon is more electronegative than hydrogen. So cleavage of (b) results in a carbanion stabilized by resonance

You can form 2 allylic (stabilized by resonance) carbanions (a and b). Which one is most stable?
 
Cleavage of a results in a vinylic carbanion. b forms the more stable allylic carbanion
 
Sorry, I read that wrong. It should have been position 'b' and 'd' produce the allylic carbanions. Which one is most stable?
 

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