MadSci Network: Chemistry |
The most commonly used definition of an acid is a substance that can lose a proton (H+ ion):
HA <===> H+ + A-
Thus, anything that makes A- (the anion) a more stable chemical species will favor the right hand side of the equilibrium, and make HA a stronger acid.
There are two primary ways to help stabilize a negative charge:
In your question, trifluoroacetic acid is a much stronger acid than acetic acid because the extremely electronegative fluorine atoms stabilize the negative charge on the trifluoroacetate anion relative to the acetate anion:
CF3COOH <===> H+ + CF3COO-
Ka = 5.9 x 10-1
CH3COOH <===> H+ + CH3COO-
Ka = 1.75 x 10-5
This discussion has ignored the effect of the solvent (usually water), polyprotic acids (capable of giving up more than one H+), and the conjugate acid of a base (e.g. NH4+). You can find out more about these topics in your textbook.
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