1. Bond-line drawings -- How to read bond-line drawings -- How to draw bond-line drawings -- Mistakes to avoid -- more exercises -- Identifying formal charges -- Finding lone pairs that are not drawn -- 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 -- Assessing the relative importance of resonance structures -- 3. Acid-base reactions -- Factor 1-what atom is the charge on? -- Factor 2-resonance -- Factor 3-induction -- Factor 4-orbitals -- Ranking the four factors -- Other factors -- Quantitative measurement (pKa values) -- Predicting the position of equilibrium -- Showing a mechanism -- 4. Geometry -- Orbitals and hybridization states -- Geometry -- Lone pairs -- 5. Nomenclature -- Functional group -- Unsaturation -- Naming the parent chain-- Naming substituents -- Stereoisomerism -- Numbering -- Common names -- Going from a name to a structure -- 6. Conformations -- How to draw a newman projection -- Ranking the stability of newman projections -- Drawing chair conformations -- Placing groups on the chair -- Ring flipping -- Comparing the stability of chairs -- Don't be confused by the nomenclature -- 7. Configurations -- Locating chiral centers -- Determining the configuration of a chiral center -- Nomenclature -- Drawing enantiomers -- Diastereomers -- Meso compounds -- Drawing fischer projections -- Optical activity -- 8. Mechanisms -- Introduction to mechanisms -- Nucleophiles and electrophiles -- Basicity vs. nucleophilisity -- Arrow-pushing patterns for ionic mechanisms -- Carbocation rearrangements -- Information contained in a mechanism -- 9. Substitution reactions -- The mechanisms -- Factor 1- the electrophile (substrate) -- Factor 2- the nucleophile -- Factor 3- the leaving group-- Factor 3- the leaving group -- Factor 4- the solvent -- Using all four factors -- Substitution reactions teach us some important lessons -- 10. Elimination reactions -- The E2 mechanisms -- The regiochemical outcome of an E2 reaction -- The stereochemical outcome of an E2 reaction -- The E1 mechanism -- The regiochemical outcome of an E1 reaction -- Thestereochemical outcome of an E1 reaction -- substitution vs. elimination -- Determining the function of the reagent -- Identifying the mechanism(s) -- Predicting the products -- 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, Markovnikov -- Adding H and OH, anti-Markovnikov -- Synthesis techniques -- Adding Br and Br; adding Br and OH -- Adding OH and OH, anti -- Adding OH and OH, syn -- Oxidative cleavage of an alkene-- Summary of reactions -- 12. alkynes -- Structure and properties of alkynes -- Preparation of alkynes -- Alkylation of terminal alkynes -- Reduction of alkynes -- Hydration of alkynes -- Keto-enol tautomerization -- Ozonolysis of alkynes -- 13. Alcohols -- Naming and designating alcohols -- Predicting solubility of alcohols -- Predicting relative acidity of alcohols acidity of alcohols -- Preparing alcohols: a review -- Preparing alcohols: a review -- Preparing alcohols via reduction -- Preparing alcohols via grignard reactions -- Summary of methods for preparing alcohols -- Reactions of alcohols: substitution and elimination -- Reactions of alcohols: oxidation -- Converting an alcohol into an ether -- 14. Ethers and epoxides -- Introduction to ethers -- Preparation of ethers -- Reactions of ethers -- Preparation of epoxides -- Ring-opening reactions of epoxides -- 15. Synthesis -- One-step syntheses -- Multistep syntheses -- Retrosynthetic analysis -- Creating your own problems.
Summary:
Is organic chemistry really as tough as everyone says it is? It's not about memorization. Like a movie, it's about making sense of the plot, the scenes, and the individual concepts that make up the story. This book reviews critical principles and explains why they are relevant to the rest of the course.
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