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Thursday, April 28, 2016

Organic Chemistry, "Function", Part 3 - The Effect of Acetic Acid Fluorination on Acid Dissociation Constant Values

Greetings,

Yet another structural effect on macroscopic properties arises when electron-withdrawing atoms are added to organic acids in place of carbon-bonded hydrogen atoms.  As more of these electron-withdrawing atoms are added, negatively charged electrons are more evenly distributed across the molecule, resulting in a more stable deprotonated acid anion.  As more electron-withdrawing groups are added the acid-strength, reported using acid dissociation constant values, dramatically increases.  This effect is shown in the following chart using acetic acid and fluorine atoms as the electron-withdrawing atom.


The reader may recall, from an earlier post, that Ka is numerically equal to the mathematical product of acid-dissociated ion molar concentrations divided by the equilibrium molarity of the intact acid molecule at equilibrium.  The chart also contains changing double arrows, to indicate the change in equilibrium position toward the product side as more fluorine atoms are added.

That's all for now.  As always, thank you for reading!


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