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• Cover
• 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
• Advertisement Page
• Connect with Dummies
• End User License Agreement