Factors That Affect Acidity (4) Electron Withdrawing Groups

by James

 

{ 4 comments… read them below or add one }

Katharine

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!

Reply

Katharine

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

Reply

Katharine

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

Reply

Thiago

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?

Reply

Leave a Comment