Chapter 1. The Basics.
1. Structure and Stability of Organic Compounds
o Conventions of Drawing Structures; Grossman's Rule
o Lewis Structures; Resonance Structures
o Molecular Shape; Hybridization o Aromaticity
2. Bronsted Acidity and Basicity
o pKa Values
o Tautomerism
3. Kinetics and Thermodynamics
4. Getting Started at Drawing a Mechanism
o Reading and balancing organic reaction equations
o Determining which bonds are made and broken in a reaction
5. Classes of Overall Transformations
6. Classes of Mechanisms
o Polar Mechanisms
§ Nucleophiles
§ Electrophiles and Leaving Groups
§ Acidic and Basic Conditions; The pKa Rule
§ A Typical Polar Mechanism
o Free-Radical Mechanisms
o Pericyclic Mechanisms
o Transition-Metal-Catalyzed and -Mediated Mechanisms
7. Summary
8. End of Chapter Problems
Chapter 2. Polar Reactions under Basic Conditions.
1. Introduction to Substitution and Elimination
o Substitution by the SN2 Mechanism
o β-Elimination by the E2 and E1cb Mechanisms o Predicting Substitution vs. Elimination
2. Addition of Nucleophiles to Electrophilic π Bonds
o Addition to Carbonyl Compounds
o Conjugate Addition; The Michael Reaction 3. Substitution at C(sp2)-X s Bonds
o Substitution at Carbonyl C
o Substitution at Alkenyl and Aryl C
o Metal Insertion; Halogen-Metal Exchange
4. Substitution and Elimination at C(sp3)-X σ Bonds o Substitution by the SRN1 Mechanism
o Substitution by the Elimination-Addition Mechanism
o Substitution by the One-Electron Transfer Mechanism
o Metal Insertion; Halogen-Metal Exchange o α-Elimination; Generation and Reactions of Carbenes
5. Base-Promoted Rearrangements
o Migrations from C to C
o Migrations from C to O
o Migrations from C to N
o Migrations from B to C or O
6. Two Multistep Reactions
o The Swern Oxidation
o The Mitsunobu Reaction 7. Summary
8. End of Chapter Problems
Chapter 3. Polar Reactions under Acidic Conditions.
1. Carbocations
o Carbocation Stability o Carbocation Generation; The Role of Protonation
o Typical Reactions of Carbocations; Rearrangements
2. Substitution and β-Elimination Reactions at C(sp3)-X
o Substitution by the SN1 and SN2 Mechanisms
o Elimination by the E1 Mecha
About the Author: Robert B. Grossman earned his A.B. degree at Princeton University and his Ph.D. at MIT. He then moved from Cambridge, Massachusetts to Cambridge, England for his postdoctoral work. In 1994, he moved from the United Kingdom (UK) to the University of Kentucky (UK), where he has been ever since. At UK, Dr. Grossman maintains an active research program focused on synthetic methodology, target-directed synthesis, and biosynthesis. He is also the creator of ACE Organic, a Web-based organic chemistry homework program. Dr. Grossman has also served two terms as one of the two faculty representatives on the UK Board of Trustees.
