Section 7.1: The ‘basic’ idea of an acid-base reaction

1. The Brønsted-Lowry definition of acidity
2. The Lewis definition of acidity

Section 7.2: Comparing the acidity and basicity of organic functional groups– the acidity constant

1. Defining K_a and pK_a
2. Using pKa values to predict reaction equilibria
3. pKa and pH: the Henderson-Hasselbalch equation

Section 7.3: Structural effects on acidity and basicity

1. Periodic trends
2. The resonance effect
3. The inductive effect

Section 7.4: More on resonance effects on acidity and basicity

1. The acidity of phenols
2. The basicity of nitrogen-containing groups: aniline, imines, pyridine, and pyrrole

Section 7.5: Carbon acids and enolate ions

Section 7.6: Polyprotic acids

Section 7.7: The effects of solvent and enzyme microenvironment on acidity

Section 7.P: Problems for Chapter 7

In the previous chapter, we introduced many of the fundamental concepts that will form the foundation of your understanding of how organic molecules react.  Now, we begin our study of organic reactivity in earnest, beginning with the simplest reaction type: the transfer of a proton from an acid to a base.  After reviewing some basic ideas about acid-base equilibria with which you are probably already familiar from General Chemistry, we will dive into some very challenging new waters, as we attempt to use our understanding of organic structure to predict how different organic functional groups are likely to react in an acid-base context.  Many of the ideas that are introduced in this chapter, though perhaps difficult to grasp as first, will be crucial to understanding not only acid base chemistry but all of the other organic reaction types that we will see throughout the remainder of the text.

Contributors

• Organic Chemistry With a Biological Emphasis by Tim Soderberg (University of Minnesota, Morris)

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