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Comparison of C-H bond energy

  • Thread starter 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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  • #2
chemisttree
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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
You can form 2 allylic (stabilized by resonance) carbanions (a and b). Which one is most stable?
 
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Cleavage of a results in a vinylic carbanion. b forms the more stable allylic carbanion
 
  • #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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