About This Book -- Foolish Assumptions -- Icons Used in This Book -- Beyond the Book -- Where to Go from Here -- pt. I Getting Started With Organic Chemistry -- ch. 1 The Wonderful World of Organic Chemistry -- Shaking Hands with Organic Chemistry -- What Are Organic Molecules, Exactly? -- An Organic Chemist by Any Other Name -- Synthetic organic chemists -- Bioorganic chemists -- Natural products chemists -- Physical organic chemists -- Organometallic chemists -- Computational chemists -- Materials chemists -- ch. 2 Dissecting Atoms: Atomic Structure and Bonding -- Electron House Arrest: Shells and Orbitals -- Electron apartments: Orbitals -- Electron instruction manual: Electron configuration -- Atom Marriage: Bonding -- To Share or Not to Share: Ionic and Covalent Bonding -- Mine! They're all mine! Ionic bonding -- The name's Bond, Covalent Bond -- Electron piggishness and electronegativity -- Separating Charge: Dipole Moments.

Problem solving: Predicting bond dipole moments -- Problem solving: Predicting molecule dipole moments -- Seeing Molecular Geometries -- Mixing things up: Hybrid orbitals -- Predicting hybridization for atoms -- It's All Greek to Me: Sigma and Pi Bonding -- ch. 3 Speaking with Pictures: Drawing Structures -- Picture-Talk: Lewis Structures -- Taking charge: Assigning formal charges -- Drawing structures -- Atom packing: Condensed structures -- Structural shorthand: Line-bond structures -- Converting Lewis structures to line-bond structures -- Determining the number of hydrogens on line-bond structures -- So lonely: Determining lone pairs on atoms -- Problem Solving: Arrow Pushing -- Drawing Resonance Structures -- Rules for resonance structures -- Problem solving: Drawing resonance structures -- Drawing more than two resonance structures -- Assigning importance to resonance structures -- Common mistakes in drawing resonance structures.

ch. 4 Covering the Bases (And the Acids) -- A Defining Moment: Acid-Base Definitions -- Arrhenius acids and bases: A little watery -- Pulling for protons: Brønsted-Lowry acids and bases -- Electron lovers and haters: Lewis acids and bases -- Comparing Acidities of Organic Molecules -- Comparing atoms -- Seeing atom hybridization -- Seeing electronegativity effects -- Seeing resonance effects -- Defining pKa: A Quantitative Scale of Acidity -- Problem Solving: Predicting the Direction of Acid-Base Reactions at Equilibrium -- ch. 5 Reactivity Centers: Functional Groups -- Hydrocarbons -- Double the fun: The alkenes -- Alkynes of fun -- Smelly compounds: The aromatics -- Singly Bonded Heteroatoms -- Happy halides -- For rubbing and drinking: Alcohols -- What stinks? Thiols -- How ethereal -- Carbonyl Compounds -- Living on the edge: Aldehydes -- Stuck in the middle: Ketones -- Carboxylic acids -- Sweet-smelling compounds: Esters.

Nitrogen-containing functional groups -- I am what I amide -- Be nice, don't be amine person -- Nitriles -- Test Your Knowledge -- ch. 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 -- Step 1 Prioritizing the substituents -- Step 2 Putting the number-four substituent in the back -- Step 3 Drawing the curve -- The Consequences of Symmetry: Meso Compounds -- Rotating Plane-Polarized Light -- Multiple Chiral Centers: Diastereomers -- Representing 3-D Structures on Paper: Fischer Projections -- Rules for using Fischer projections -- Determining R/S configuration from a Fischer projection -- Seeing stereoisomerism with Fischer projections -- Spotting meso compounds with Fischer projections.

Keeping the Jargon Straight -- pt. II Hydrocarbons -- ch. 7 What's in a Name? Alkane Nomenclature -- All in a Line: Straight-Chain Alkanes -- Reaching Out: Branching Alkanes -- Finding the longest chain -- Numbering the chain -- Seeing the substituents -- Ordering the substituents -- More than one of a kind -- Naming complex substituents -- ch. 8 Drawing Alkanes -- Converting a Name to a Structure -- Conformation of Straight-Chain Alkanes -- Newman! Conformational analysis and Newman projections -- Conformations of butane -- Full Circle: Cycloalkanes -- The stereochemistry of cycloalkanes -- Conformations of cyclohexane -- Problem Solving: Drawing the Most Stable Chair Conformation -- Reacting Alkanes: Free-Radical Halogenation -- Getting things started: Initiation -- Keeping the reaction going: Propagation -- You're fired: Termination steps -- Selectivity of chlorination and bromination -- ch. 9 Seeing Double: The Alkenes -- Defining Alkenes.

Taking Away Hydrogens: Degrees of Unsaturation -- Determining degrees of unsaturation from a structure -- Problem solving: Determining degrees of unsaturation from a molecular formula -- The Nomenclature of Alkenes -- Numbering the parent chain -- Adding multiple double bonds -- Common names of alkenes -- The Stereochemistry of Alkenes -- You on my side or their side? Cis and trans stereochemistry -- Playing a game of high-low: E/Z stereochemistry -- Stabilities of Alkenes -- Alkene substitution -- Stability of cis and trans isomers -- Formation of Alkenes -- Elimination of acid: Dehydrohalogenation -- Losing water: Dehydration of alcohols -- Alkenes from coupling: The Wittig reaction -- ch. 10 Reactions of Alkenes -- Adding Hydrohalic Acids across Double Bonds -- I'm Positive: Carbocations -- Helping a neighbor: Hyperconjugation -- Resonance stabilization of carbocations -- Carbocation mischief: Rearrangements -- Adding Water across Double Bonds.

Markovnikov addition: Oxymercuration-demercuration -- Anti-Markovnikov addition: Hydroboration -- A double shot: Dihydroxylation -- Double the fun: Bromination -- 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 -- ch. 11 It Takes Alkynes: The Carbon-Carbon Triple Bond -- Naming Alkynes -- Seeing Alkyne Orbitals -- Alkynes in Rings -- Making Alkynes -- Losing two: Dehydrohalogenation -- Coupling alkynes: Acetylide chemistry -- Brominating alkynes: Double the fun -- Saturating alkynes with hydrogen -- Adding one hydrogen molecule to alkynes -- Oxymercuration of alkynes -- Hydroboration of alkynes -- pt. III Functional Groups -- ch. 12 Replacing and Removing: Substitution and Elimination Reactions -- Group Swap: Substitution Reactions.

Seeing Second-Order Substitution: The SN2 Mechanism -- How fast? The rate equation for the SN2 reaction -- Effect of the substrate on the SN2 reaction -- Needs nucleus: The role of the nucleophile -- Seeing the SN2 reaction in 3-D: Stereochemistry -- Seeing solvent effects -- I'm outta here: The leaving group -- First-Order Substitution: The SN1 Reaction -- How fast? The rate equation for the SN1 reaction -- Seeing good SN1 substrates -- Seeing solvent effects on the SN1 reaction -- Stereochemistry of the SN1 reaction -- Other fun facts about the SN1 reaction -- Seeing Elimination Reactions -- Seeing second-order eliminations: The E2 reaction -- Seeing first-order elimination: The E1 reaction -- Help! Distinguishing Substitution from Elimination -- ch. 13 Getting Drunk on Organic Molecules: The Alcohols -- Classifying Alcohols -- An Alcohol by Any Other Name: Naming Alcohols -- Alcohol-Making Reactions -- Adding water across double bonds.

Reduction of carbonyl compounds -- The Grignard reaction -- Reactions of Alcohols -- Losing water: Dehydration -- Making ethers: Williamson ether synthesis -- Oxidation of alcohols -- ch. 14 Side-by-Side: Conjugated Alkenes and the Diels--Alder Reaction -- Seeing Conjugated Double Bonds -- Addition of Hydrohalic Acids to Conjugated Alkenes -- Seeing the reaction diagram of conjugate addition -- Comparing kinetics and thermodynamics of conjugate addition -- The Diels--Alder Reaction -- Seeing the diene and the dienophile -- The stereochemistry of addition -- Seeing bicyclic products -- Problem Solving: Determining Products of Diels--Alder Reactions -- ch. 15 Lord of the Rings: Aromatic Compounds -- Defining Aromatic Compounds -- The structure of benzene -- Diversity of aromatic compounds -- So, what exactly makes a molecule aromatic? -- Huckel's 4n + 2 rule -- Explaining Aromaticity: Molecular Orbital Theory -- What the heck is molecular orbital theory?

Making molecular orbital diagrams -- Two rings diverged in a wood: Frost circles -- Making the molecular orbital diagram of benzene -- Seeing the molecular orbitals of benzene -- Making the molecular orbital diagram of cyclobutadiene -- Problem Solving: Determining Aromaticity -- Problem Solving: Predicting Acidities and Basicities -- Comparing acidities -- Comparing basicities -- Naming Benzenes and Aromatics -- Common names of substituted benzenes -- Names of common aromatics -- ch. 16 Bringing Out the Howitzers: Reactions of Aromatic Compounds -- Electrophilic Aromatic Substitution of Benzene -- Adding alkyl substituents: Friedel--Crafts alkylation -- Overcoming adversity: Friedel--Crafts acylation -- Reducing nitro groups -- Oxidation of alkylated benzenes -- Adding Two: Synthesis of Disubstituted Benzenes -- Electron donors: Ortho-para activators -- Electron-withdrawing groups: Meta directors -- Problem Solving: Synthesis of Substituted Benzenes.

Nucleophiles Attack! Nucleophilic Aromatic Substitution -- pt. IV Spectroscopy and Structure Determination -- ch. 17 A Smashing Time: Mass Spectrometry -- Defining Mass Spectrometry -- Taking Apart a Mass Spectrometer -- The inlet -- Electron ionization: The smasher -- The sorter and weigher -- Detector and spectrum -- 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 -- Smashing alkanes -- Breaking next to a heteroatom: Alpha cleavage -- Loss of water: Alcohols -- Rearranging carbonyls: The McLafferty rearrangement -- Breaking benzenes and double bonds -- Self test: Working the problem -- Key Ideas Checklist -- ch. 18 Seeing Good Vibrations: IR Spectroscopy -- Bond Calisthenics: Infrared Absorption -- Applying Hooke's law to molecules -- Seeing bond vibration and IR light absorption.

Seeing absorption intensity -- IR forbidden stretches -- Dissecting an IR Spectrum -- Identifying the Functional Groups -- Sizing up the IR spectrum -- Recognizing functional groups -- Seeing to the Left of the C-H Absorptions -- Big and fat: The alcohols -- Milking the spectrum: Amines -- Seeing to the Right of the C-H Absorptions -- Big and tall: Carbonyl groups -- Hydrocarbon stretches: Alkenes, alkynes, and aromatics -- ch. 19 NMR Spectroscopy: Hold onto Your Hats, You're Going Nuclear! -- Why NMR? -- How NMR Works -- Giant magnets and molecules: NMR theory -- Grab your jackets: Electron shielding -- The NMR Spectrum -- Standardizing chemical shifts -- Seeing symmetry and chemical equivalency -- The NMR Spectrum Manual: Dissecting the Pieces -- Seeing the chemical shift -- Incorporating the integration -- Catching on to coupling -- Considering Carbon NMR -- Checklist: Putting the Pieces Together.

ch. 20 Following the Clues: Solving Problems in NMR -- Follow the Clues -- Clue 1 Determine the degrees of unsaturation from the molecular formula -- Clue 2 Look at the IR spectrum to determine the major functional groups present in the unknown compound -- Clue 3 Determine the peak ratios by measuring the heights of the integration curves -- Clue 4 Break the NMR peaks into fragments using the integration from Clue 3 -- Clue 5 Combine the fragments in a way that fits with the NMR peak splitting, the chemical shift, and the degrees of unsaturation -- Clue 6 Recheck your structure with the NMR and the IR spectrum to make sure it's an exact match -- Working Problems -- Example 1 Using the molecular formula and NMR to deduce the structure of a molecule -- Example 2 Using the molecular formula, IR, and NMR to deduce the structure of a molecule -- Three Common Mistakes in NMR Problem Solving.

Mistake #1 Trying to determine a structure from the chemical shift -- Mistake #2 Starting with coupling -- Mistake #3 Confusing integration with coupling -- pt. V The Part of Tens -- ch. 21 Ten (Or So) Great Organic Chemists -- August Kekule -- Friedrich Wohler -- Archibald Scott Couper -- Johan Josef Loschmidt -- Louis Pasteur -- Emil Fischer -- Percy Julian -- Robert Burns Woodward -- Linus Pauling -- Dorothy Hodgkin -- John Pople -- ch. 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 -- ch. 23 Ten Cool Organic Molecules -- Octanitrocubane -- Fenestrane -- Carbon Nanotubes -- Bullvalene -- The Norbornyl Cation -- Capsaicin -- Indigo -- Maitotoxin -- Molecular Cages -- Fucitol -- Par VI Appendixes -- Appendix A Working Multistep Synthesis Problems -- Why Multistep Synthesis?

Five Commandments -- Commandment 1 Thou shalt learn thy reactions -- Commandment 2 Thou shalt compare carbon skeletons -- Commandment 3 Thou shalt work backward -- Commandment 4 Thou shalt check thyne answer -- Commandment 5 Thou shalt work many problems -- Appendix B Working Reaction Mechanisms -- The Two Unspoken Mechanism Types -- Do's and Don'ts for Working Mechanisms -- Types of Mechanisms -- Appendix C Glossary.