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Comparison of C-H bond energy

  1. Apr 18, 2009 #1
    1. The problem statement, all variables and given/known data
    Look at the diagram accompanying the question. Which has least C-H bond energy?


    3. 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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  3. Apr 22, 2009 #2

    chemisttree

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    You can form 2 allylic (stabilized by resonance) carbanions (a and b). Which one is most stable?
     
  4. Apr 22, 2009 #3
    Cleavage of a results in a vinylic carbanion. b forms the more stable allylic carbanion
     
  5. Apr 23, 2009 #4

    chemisttree

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    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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