Organic Chemistry I for Dummies.

Intro
Table of Contents
Introduction
About This Book
Foolish Assumptions
Icons Used in This Book
Beyond the Book
Where to Go from Here
Part 1: Getting Started with Organic Chemistry
Chapter 1: The Wonderful World of Organic Chemistry
Shaking Hands with Organic Chemistry
What Are Organic Molecules, Exactly?
An Organic Chemist by Any Other Name …
Chapter 2: Dissecting Atoms: Atomic Structure and Bonding
Electron House Arrest: Shells and Orbitals
Atom Marriage: Bonding
To Share or Not to Share: Ionic and Covalent Bonding
Separating Charge: Dipole Moments
Seeing Molecular Geometries
It's All Greek to Me: Sigma and Pi Bonding
Chapter 3: Speaking with Pictures: Drawing Structures
Picture-Talk: Lewis Structures
Problem Solving: Arrow Pushing
Drawing Resonance Structures
Chapter 4: Covering the Bases (And the Acids)
A Defining Moment: Acid-Base Definitions
Comparing Acidities of Organic Molecules
Defining pKa: A Quantitative Scale of Acidity
Problem Solving: Predicting the Direction of Acid-Base Reactions at Equilibrium
Chapter 5: Reactivity Centers: Functional Groups
Hydrocarbons
Singly Bonded Heteroatoms
Carbonyl Compounds
Test Your Knowledge
Chapter 6: Seeing in 3-D: Stereochemistry
Drawing Molecules in 3-D
Comparing Stereoisomers and Constitutional Isomers
Mirror Image Molecules: Enantiomers
Seeing Chiral Centers
Assigning Configurations to Chiral Centers: The R/S Nomenclature
Problem Solving: Determining R/S Configuration
The Consequences of Symmetry: Meso Compounds
Rotating Plane-Polarized Light
Multiple Chiral Centers: Diastereomers
Representing 3-D Structures on Paper: Fischer Projections
Keeping the Jargon Straight
Part 2: Hydrocarbons
Chapter 7: What's in a Name? Alkane Nomenclature.

All in a Line: Straight-Chain Alkanes
Reaching Out: Branching Alkanes
Chapter 8: Drawing Alkanes
Converting a Name to a Structure
Conformation of Straight-Chain Alkanes
Full Circle: Cycloalkanes
Problem Solving: Drawing the Most Stable Chair Conformation
Reacting Alkanes: Free-Radical Halogenation
Chapter 9: Seeing Double: The Alkenes
Defining Alkenes
Taking Away Hydrogens: Degrees of Unsaturation
The Nomenclature of Alkenes
The Stereochemistry of Alkenes
Stabilities of Alkenes
Formation of Alkenes
Chapter 10: Reactions of Alkenes
Adding Hydrohalic Acids across Double Bonds
I'm Positive: Carbocations
Adding Water across Double Bonds
Chopping Up Double Bonds: Ozonolysis
Double-Bond Cleavage: Permanganate Oxidation
Making Cyclopropanes with Carbenes
Making Cyclopropanes: The Simmons-Smith Reaction
Making Epoxides
Adding Hydrogen: Hydrogenation
Chapter 11: It Takes Alkynes: The Carbon-Carbon Triple Bond
Naming Alkynes
Seeing Alkyne Orbitals
Alkynes in Rings
Making Alkynes
Part 3: Functional Groups
Chapter 12: Replacing and Removing: Substitution and Elimination Reactions
Group Swap: Substitution Reactions
Seeing Second-Order Substitution: The SN2 Mechanism
First-Order Substitution: The SN1 Reaction
Seeing Elimination Reactions
Help! Distinguishing Substitution from Elimination
Chapter 13: Getting Drunk on Organic Molecules: The Alcohols
Classifying Alcohols
An Alcohol by Any Other Name: Naming Alcohols
Alcohol-Making Reactions
Reactions of Alcohols
Chapter 14: Side-by-Side: Conjugated Alkenes and the Diels-Alder Reaction
Seeing Conjugated Double Bonds
Addition of Hydrohalic Acids to Conjugated Alkenes
The Diels-Alder Reaction
Problem Solving: Determining Products of Diels-Alder Reactions.

Chapter 15: Lord of the Rings: Aromatic Compounds
Defining Aromatic Compounds
Explaining Aromaticity: Molecular Orbital Theory
Problem Solving: Determining Aromaticity
Problem Solving: Predicting Acidities and Basicities
Naming Benzenes and Aromatics
Chapter 16: Bringing Out the Howitzers: Reactions of Aromatic Compounds
Electrophilic Aromatic Substitution of Benzene
Adding Two: Synthesis of Disubstituted Benzenes
Problem Solving: Synthesis of Substituted Benzenes
Nucleophiles Attack! Nucleophilic Aromatic Substitution
Part 4: Spectroscopy and Structure Determination
Chapter 17: A Smashing Time: Mass Spectrometry
Defining Mass Spectrometry
Taking Apart a Mass Spectrometer
The Mass Spectrum
Kind and Caring: Sensitivity of Mass Spec
Resolving the Problem: Resolution
Changing the Weight: Isotopes
The Nitrogen Rule
Identifying Common Fragmentation Patterns
Key Ideas Checklist
Chapter 18: Seeing Good Vibrations: IR Spectroscopy
Bond Calisthenics: Infrared Absorption
Dissecting an IR Spectrum
Identifying the Functional Groups
Seeing to the Left of the C-H Absorptions
Seeing to the Right of the C-H Absorptions
Chapter 19: NMR Spectroscopy: Hold onto Your Hats, You're Going Nuclear!
Why NMR?
How NMR Works
The NMR Spectrum
The NMR Spectrum Manual: Dissecting the Pieces
Considering Carbon NMR
Checklist: Putting the Pieces Together
Chapter 20: Following the Clues: Solving Problems in NMR
Follow the Clues
Working Problems
Three Common Mistakes in NMR Problem Solving
Part 5: The Part of Tens
Chapter 21: Ten (Or So) Great Organic Chemists
August Kekulé
Friedrich Wöhler
Archibald Scott Couper
Johan Josef Loschmidt
Louis Pasteur
Emil Fischer
Percy Julian
Robert Burns Woodward
Linus Pauling
Dorothy Hodgkin
John Pople.

Chapter 22: Ten Cool Organic Discoveries
Explosives and Dynamite!
Fermentation
The Synthesis of Urea
The Handedness of Tartaric Acid
Diels-Alder Reaction
Buckyballs
Soap
Aspartame
Penicillin
Teflon
Chapter 23: Ten Cool Organic Molecules
Octanitrocubane
Fenestrane
Carbon Nanotubes
Bullvalene
The Norbornyl Cation
Capsaicin
Indigo
Maitotoxin
Molecular Cages
Fucitol
Part 6: Appendixes
Appendix A: Working Multistep Synthesis Problems
Why Multistep Synthesis?
The Five Commandments
Appendix B: Working Reaction Mechanisms
The Two Unspoken Mechanism Types
Do's and Don'ts for Working Mechanisms
Types of Mechanisms
Appendix C: Glossary
About the Author
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