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
Natural products chemists
Physical organic chemists
ch. 2 Dissecting Atoms: Atomic Structure and Bonding
Electron House Arrest: Shells and Orbitals
Electron apartments: Orbitals
Electron instruction manual: Electron configuration
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
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: Br©ınsted-Lowry acids and bases
Electron lovers and haters: Lewis acids and bases
Comparing Acidities of Organic Molecules
Seeing atom hybridization
Seeing electronegativity 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
Double the fun: The alkenes
Smelly compounds: The aromatics
Singly Bonded Heteroatoms
For rubbing and drinking: Alcohols
Living on the edge: Aldehydes
Stuck in the middle: Ketones
Sweet-smelling compounds: Esters.
Nitrogen-containing functional groups
Be nice, don't be amine person
ch. 6 Seeing in 3-D: Stereochemistry
Comparing Stereoisomers and Constitutional Isomers
Mirror Image Molecules: Enantiomers
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
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
ch. 7 What's in a Name? Alkane Nomenclature
All in a Line: Straight-Chain Alkanes
Reaching Out: Branching Alkanes
Finding the longest chain
Ordering the substituents
Naming complex substituents
Converting a Name to a Structure
Conformation of Straight-Chain Alkanes
Newman! Conformational analysis and Newman projections
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
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
The Stereochemistry of Alkenes
You on my side or their side? Cis and trans stereochemistry
Playing a game of high-low: E/Z stereochemistry
Stability of cis and trans isomers
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
Adding Hydrogen: Hydrogenation
ch. 11 It Takes Alkynes: The Carbon-Carbon Triple Bond
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
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
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
An Alcohol by Any Other Name: Naming Alcohols
Adding water across double bonds.
Reduction of carbonyl compounds
Losing water: Dehydration
Making ethers: Williamson ether synthesis
ch. 14 Side-by-Side: Conjugated Alkenes and the Diels
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
Seeing the diene and the dienophile
The stereochemistry of addition
Problem Solving: Determining Products of Diels
ch. 15 Lord of the Rings: Aromatic Compounds
Defining Aromatic Compounds
Diversity of aromatic compounds
So, what exactly makes a molecule aromatic?
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
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
Overcoming adversity: Friedel
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
Electron ionization: The smasher
Kind and Caring: Sensitivity of Mass Spec
Resolving the Problem: Resolution
Changing the Weight: Isotopes
Identifying Common Fragmentation Patterns
Breaking next to a heteroatom: Alpha cleavage
Rearranging carbonyls: The McLafferty rearrangement
Breaking benzenes and double bonds
Self test: Working the problem
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
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!
Giant magnets and molecules: NMR theory
Grab your jackets: Electron shielding
Standardizing chemical shifts
Seeing symmetry and chemical equivalency
The NMR Spectrum Manual: Dissecting the Pieces
Seeing the chemical shift
Incorporating the integration
Checklist: Putting the Pieces Together.
ch. 20 Following the Clues: Solving Problems in NMR
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
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
ch. 21 Ten (Or So) Great Organic Chemists
ch. 22 Ten Cool Organic Discoveries
The Handedness of Tartaric Acid
ch. 23 Ten Cool Organic Molecules
Appendix A Working Multistep Synthesis Problems
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
