Factors That Affect Acidity (4) Electron Withdrawing Groups

by James

 

{ 3 comments… read them below or add one }

Katharine 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
Cl F |
HO \ / OH (not sure if that’s clear) —> HO–C–C–C–OH
\/\/ |
F

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?)

Thanks!

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Katharine April 13, 2013 at 10:39 pm

Ok—my lame attempt at a bond line drawing definitely got mangled. Sorry! :(

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Katharine April 13, 2013 at 10:51 pm

Sorry again…there should be a fluorine and a chlorine attached to the central carbon.

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