Organic Chemistry I as a Second LanguageTM: Translating the Basic Concepts, 2nd Edition
June 2007, ©2008
Building upon the success of the first edition and feedback, the new edition continues to be written in a way that shows the patterns in organic chemistry so that readers can gain a deeper conceptual understanding of the material. Topics are presented clearly in a casual writing style along with numerous hands-on problem solving exercises.
Chapter 1. Bond-Line Drawings.
How to Read Bond-Line Drawings.
How to Draw Bond-Line Drawings.
Mistakes to Avoid.
Identifying Formal Charges.
Finding Lone Pairs That Are Not Drawn.
Chapter 2. Resonance.
What Is Resonance?
Curved Arrows: The Tools for Drawing Resonance Structures.
The Two Commandments.
Drawing Good Arrows.
Formal Charges in Resonance Structures.
Drawing Resonance Structures--Step by Step.
Drawing Resonance Structures--By Recognizing Patterns.
A Lone Pair Next to a Pi Bond.
A Lone Pair Next to a Positive Charge.
A Pi Bond Next to a Positive Charge.
A Pi Bond Between Two Atoms, Where One of Those Atoms Is
Electronegative (N, O, etc.).
Pi Bonds Going All the Way Around a Ring.
Assessing the Relative Importance of Resonance Structures.
Chapter 3. Acid-Base Reactions.
Factor 1--What Atom Is the Charge on?
Ranking the Four Factors.
Quantitative Measurement (pKa values).
Predicting the Position of Equilibrium.
Showing a Mechanism.
Chapter 4. Geometry.
Orbitals and Hybridization States.
Chapter 5. Nomenclature.
Naming the Parent Chain.
Going from a Name to a Structure.
Chapter 6. Conformations.
How to Draw a Newman Projection.
Ranking the Stability of Newman Projections.
Drawing Chair Conformations.
Placing Groups on the Chair.
Comparing the Stability of Chairs.
Don't Be Confused by the Nomenclature.
Chapter 7. Configurations.
Determining the Configuration of a Stereocenter.
Drawing Fischer Projections.
Chapter 8. Mechanisms.
Arro w Pushing.
Nucleophiles and Electrophiles.
Bases Versus Nucleophiles.
The Regiochemistry Is Contained Within the Mechanism.
The Stereochemistry Is Contained Within the Mechanism.
A List of Mechanisms.
Chapter 9. Substitution Reactions.
Factor 1--The Electrophile (Substrate).
Factor 2--The Nucleophile.
Factor 3--The Leaving Group.
Factor 4--The Solvent.
Using All Four Factors.
Substitution Reactions Teach Us Some Important Lessons.
Chapter 10. Elimination Reactions.
Mechanisms (E1 and E2).
Factor 1--The Substrate.
Factor 2--The Base.
Factor 3--The Leaving Group.
Factor 4--Solvent Effects.
Using All of the Factors.
Elimination Reactions--Regiochemistry and Stereochemistry.
Chapter 11. Addition Reactions.
Terminology Describing Regiochemistry.
Terminology Describing Stereochemistry.
Adding H and H.
Adding H and X, Markovnikov.
Adding H and Br, Anti-Markovnikov.
Adding H and OH, Markovnikov.
Adding H and OH, Anti-Markovnikov.
Adding Br and Br; Adding Br and OH.
Adding OH and OH, Anti.
Adding OH and OH, Syn.
Oxidati ve Cleavage of an Alkene.
Chapter 12. Predicting Products.
General Tips for Predicting Products.
Substitution Versus Elimination Reactions.
Chapter 13. Synthesis.
Creating Your Own Problems.
The chapter covering Resonance has been revised
A full chapter covering alkene addition reactions has been added
- Presents the fundamental topics clearly with an informal, friendly tone
- Teaches the how-to of problem solving including approaching problems strategically
- Shows the relationship between concepts and puts topics in context