Master Organic Chemistry
April 13, 2013 at 10:38 pm
What happens when there are two halogens attached to a central carbon atom? Is the hydrogen closest to the more electronegative halogen the most acidic hydrogen because the inductive effect will be slightly stronger? For example:
Cl F |
HO \ / OH (not sure if that’s clear) —> HO–C–C–C–OH
or, because of the tetrahedral geometry about the central carbon, are both hydrogens equally acidic? (If that’s true, aren’t the halogen-involved bond angles greater than 109.5 degrees because of their electronegativity?)
April 13, 2013 at 10:39 pm
Ok—my lame attempt at a bond line drawing definitely got mangled. Sorry! :(
April 13, 2013 at 10:51 pm
Sorry again…there should be a fluorine and a chlorine attached to the central carbon.
February 4, 2016 at 9:24 am
There is one thing I don’t understand. Why do that high electronegativity of the substituent does make the base more stable and therefore its conjugate acid more acid, why can’t you say that the substituent also makes the acid itself more stable, therefore its conjugate base is weak?
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