1. University of California,
Chapter 2
Acids and Bases:
Central to Understanding Organic Chemistry
Paula Yurkanis Bruice
University of California,
Santa Barbara

2. Acids and Bases in Organic Reactions
H’s in organic compounds have varying degrees of acidity
Chapter 2

3. Electronegativity Affects pKa Values
When atoms are the same size, the strongest acid has
its hydrogen attached to the most electronegative atom.

4. the Weaker Its Conjugate Base
The Stronger the Acid,
the Weaker Its Conjugate Base
stable bases are weak bases

5. Acidity and Structure Electronegative atoms or groups increase acidity
Chapter 2

6. The equilibrium favors formation of the weaker acid.
The Position of Equilibrium
The equilibrium favors formation of the weaker acid.

7. pKa as a Stability ParameterD
acid 
H+ + base
pKaDGº
pKa tracks relative potential E of conj base
Strong acids: low pKa = stable conj base
Weak acids: high pKa = unstable conj base
Chapter 2

8. Examples of Organic Acid - Base Reactions
To use pKa as a PE write it under base form
Rxn shifts to side with lowest PE
Textbook shows pKa values under acids
Chapter 2

9. Relative Amounts of Different Forms of a Compound
pH tracks potential energy of acid form of a compound relative to conjugate base form of same compound
Chapter 2