Acid Strength Trends and Conjugate Base Stability

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This entire section will deal with Brønsted-Lowry acids and bases.  In other words, the simple model of HA where the “H” is a proton and the “A” is the base.

When you here the word “conjugate”, it means the product AFTER the proton is donated.  The conjugate acid is the newly protonated product; the conjugate base is the leftover “A” AFTER the proton leaves.

 

 

The “H” is either strongly bound to the base “A” or loosely bound.

Here’s how to tell:

Protons are more acidic when the conjugate base is more stable.

How can I tell if it is more stable as a conjugate base?
-Electronegativity
-Resonance

ELECTRONEGATIVITY – fancy way to say how evenly electrons are shared in a bond.

Fluorine does not like to share electrons, so HF is a strong acid since F is the most electronegative, but wait…

As the size of the conjugate base becomes larger, the stability of the conjugate base increases.  Bromine is a huge atom, so the conjugate base “Br-“ is very stable when compared to “F-“.  Therefore, HBr is a stronger acid.  The trend continues to HI.

 

RESONANCE – fancy way to say how evenly electron charge is distributed on a molecule.  

You may have heard the term delocalized electrons.  Well, that’s electrons that aren’t localized (concentrated) at a single point.

The more you can spread that charge around, the more stable the conjugate base.

Highly recommend practicing these problems:

Acids and Bases

Resonance