anonymous
  • anonymous
Fun tricky question. Alcohol hydrogens are more acidic than alkane hydrogens. So why are bond dissociation energies of an O-H bond higher than a C-H bond? Good luck and medal + fan to ya if you get it! :P Feel free to post any ideas you have, I'll post the answer by tomorrow if no one gets it.
Chemistry
schrodinger
  • schrodinger
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Photon336
  • Photon336
More acidic, I guess because acidity depends on the stability of the resulting ion. If the ion is more stable then it will probably be more willing to give up a hydrogen. The better the acid the more stable it's conjugate base will be. The alcohol would be more stable than say the carbanion formed from say ch4 if that were possible. There are a number of things that acidity depends on and if we rank them it's a good menemonic called ARIO atom, resonance, induction, orbitals, we consider the atom first the. Resonance and so on and so forth for ranking acidity. ROH ----> RO- ch4 ---> ch3-
Photon336
  • Photon336
Bond dissociation energy for OH vs CH Generally if the O-H bond is more acidic it should imply that the bond is easier to break than a CH bond. But based off of your question, this seems like the opposite. OH bond is harder to break. I think that it could be the electronegativity difference though it's probably not that simple.
anonymous
  • anonymous
Aha you've at least understood why this is tricky, there's something at play here. Actually the reason has to do with something very subtle here. There is a trick here being made, this comparison is actually illegitimate.

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Photon336
  • Photon336
Wait
Photon336
  • Photon336
Bond dissociation = homolitic cleavage But OH bond isn't cleaved homolitically Because you get OH ---> O- + H^+ This is all I've got let's see what other people say
anonymous
  • anonymous
Yep you got it, that was the trick good job. :D

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