Includes index.

"Each chapter contains strategically positioned sections that cover important skills. In each section, an important skill is developed or fine-tuned. Multiple problems are then provided in order to build competence in that skill. Students are given the opportunity to master each core skill before moving on to the next section. The end-of-chapter exercises integrate the skills developed throughout the chapter. Three short chapters (Chapters 7, 12, and 24) are devoted entirely to skill development (proposing mechanisms and proposing syntheses). WileyPLUS incorporates hundreds of end of chapter problems all of which are available with multiple forms of problem solving support (link to text, tutorials, videos, etc.). Dr. Klein's writing style strikes a unique balance between a formal and conversational tone, while not comprising the scientific rigor expected of a 2-semester organic chemistry text."-- 1. A review of general chemistry : electrons, bonds, and molecular properties -- Introduction to organic chemistry -- Structural theory of matter -- Electrons, bonds, and Lewis structures -- Induction and polar covalent bonds -- Electrostatic potential maps -- Atomic orbitals -- Valence bond theory -- Molecular orbital theory -- Hybridized atomic orbitals -- VSEPR theory : predicting geometry -- Dipole moments and molecular polarity -- Intermolecular forces and physical properties -- Biomimicry and gecko feet -- Drug-receptor interactions -- 2. Molecular representations -- Bond-line structures -- Functional groups -- Carbon atoms with formal changes -- Identifying lone pairs -- Three-dimensional bond-line structures -- Pharmacophore -- Introduction to resonance -- Curved arrows -- Resonance structures -- Delocalized and localized lone pairs -- 3. Acids and bases -- Br²nsted-Lowry acids and bases -- Flow of electron density : curved arrow notation -- Antacids and heartburn -- Position of equilibrium and choice of reagents -- Solvent -- Solvating effects -- Counterions -- Baking soda versus baking powder -- Lewis acids and bases -- 4. Alkanes and cycloalkanes -- Pheromones : chemical messengers -- Isomeric alkanes -- Polymers -- Drawing Newman projections -- Conformational analysis of ethane and propane -- Analysis of butane -- Drugs and their conformations -- Cyclohexane -- Drawing chair conformations -- Stereoisomerism -- Polycyclic systems -- 5. Stereoisomerism -- Sense of smell -- designating configuration using the Cahn-Ingold Prelog system -- Chiral drugs -- Optical activity -- Stereoisomeric relationships : enantiomers and diastereomers -- Symmetry and chirality -- Fischer projections -- Conformationally mobile systems -- Resolution of enantiomers -- 6. Chemical reactivity and mechanisms -- Enthalpy -- Entrophy -- Gibbs free energy -- Explosives -- Equilibria -- Kinetics -- Nitroglycerin : an explosive with medicinal properties -- Beer-making -- Energy diagrams -- Nucleophiles and electrophiles -- Mechanisms and arrow pushing -- Combining the patterns of arrow pushing -- Drawing curved arrows -- Carbocation rearrangements -- 7. Substitution reactions -- Alkyl halides -- Pharmacology and drug design -- 8. Alkenes: structure and preparation via elimination reactions -- Alkenes in nature and in industry -- Pheromones to control insect population -- Nomenclature of alkenes -- Stereoisomerism in alkenes -- Alkene stability -- E2 mechanism -- Substitution vs. elimination -- 9. Additional reactions of alkenes -- Addition vs. elimination : a thermodynamic perspective -- Hydrohalogenation -- Cationic polymerization and polystyrene -- Acid-catalyzed hydration -- Industrial production of ethanol -- Oxymercuration-demercuration -- Hydroboration-oxidation -- Catalytic hydrogenation -- Partially hydrogenated fats and oils -- Halogenation and halohydrin formation -- Anti dihydroxylation -- Syn dihydroxylation -- Oxidative cleavage -- Predicting products of an addition reaction. 10. Alkynes -- The role of molecular rigidity -- Conducting organic polymers -- Nomenclature of alkynes -- Acidity of acetylene and terminal alkynes -- Preparation of alkynes -- Reduction of alkynes -- Hydrohalogenation of alkynes -- Hydration of alkynes -- Halogenation of alkynes -- Ozonolysis of alkynes -- Alkylation of terminal alkynes -- 11. Radical reactions -- Radicals -- Common patterns in radical mechanisms -- Chlorination of methane -- Thermodynamic considerations for halogenation reactions -- Regioselectivity of halogenation -- Stereochemistry of halogenation -- Allylic bromination -- Atmospheric chemistry and the ozone layer -- Fighting fires with chemicals -- Autooxidation and antioxidants -- Anti-Markovnikov addition -- Radical polymerization -- Radical processes in the petrochemical industry -- Halogenation as a synthetic technique -- 12. Synthesis -- One-step syntheses -- Functional group transformations -- Reactions that change the carbon skeleton -- Vitamins -- Retrosynthetic analysis -- 13. Alcohols and phenols -- Structure and properties of alcohols -- Chain length as a factor in drug design -- Acidity of alcohols and phenols -- Preparation of alcohols via reduction or addition -- Preparation of diols -- Antifreeze -- Preparation of alcohols via Grignard Reagents -- Protection of alcohols -- Preparation of phenols -- Phenols as antifungal agents -- Reactions of alcohols : substitution and elimination -- Drug metabolism -- Reactions of alcohols : oxidation -- Breath tests to measure blood alcohol level -- Biological redox reactions -- Biological oxidation of methanol and ethanol -- Oxidation of phenol -- 14. Ethers and epoxided : thiols and sulfides -- Ethers as inhalation anesthetics -- Crown ethers -- Polyether antibiotics -- Epothilones as novel anticancer agents -- Active metabolites and drug interactions -- Enantioselective epoxidation -- Ring-opening reactions of epoxides -- Ethylene oxide as a sterilizing agent for sensitive medical equipment -- Cigarette smoke and carcinogenic epoxides -- 15. Infrared spectroscopy -- Microwave ovens -- Thermal imaging for cancer detection -- Signal characteristics : wavenumber -- Signal characteristics : intensity -- IR spectroscopy for testing blood alcohol levels -- Signal characteristics : shape -- Analyzing an IR spectrum -- Using IR spectroscopy to distinguish between two compounds -- Mass spectrometry for detecting explosives -- High resolution mass spectrometry -- Gas chromatography : mass spectrometry -- Mass spectrometry of large biomolecules -- Hydrogen deficiency index : degrees of unsaturation -- 16. Nuclear magnetic resonance spectroscopy -- NMR spectroscopy -- Number of signals -- Chemical shift -- Integration -- Multiplicity -- Detection of impurities in heparin sodium -- Magnetic Resonance Imaging (MRI) -- 17. Conjugated pi systems and pericylic reactions -- Classes of dienes -- Conjugated dienes -- Molecular orbital theory -- Electrophilic addition -- Thermodynamic control vs. kinetic control -- Natural and synthetic rubbers -- An introduction to pericyclic reactions -- Diels-Alder reactions -- MO description of cycloadditions -- Electrocyclic reactions -- Sigmatropic rearrangements -- The photoinduced biosynthesis of vitamin D -- UV-VIS spectroscopy -- Sunscreens -- color -- Bleach -- The chemistry of vision -- 18. Aromatic compounds -- What is coal? -- Benzene derivatives -- Molecular cages -- Aromatic compounds other than benzene -- The development of nonsedating antihistamines -- Reactions at the benzylic position -- Reduction of the aromatic moiety -- Spectroscopy of aromatic compounds -- Buckyballs and nanotubes. 19. Aromatic substitution reactions -- Electrophilic aromatic substitution -- Halogenation -- Halogenation in drug design -- Sulfonation -- What are those colors in fruity pebbles? -- Nitration -- Friedel-Crafts alkylation -- The discovery of prodrugs -- Friedel-Crafts acylation -- Activating groups -- Deactivating groups -- Halogens : the exception -- Determining the directing effects of a substituent -- Multiple substituents -- Nucleophilic aromatic substitution -- Elimination-addition -- The mechanism of an aromatic substitution reaction -- 20. Aldehydes and ketones -- Nucleophilic addition reactions -- Oxygen nucleophiles -- Acetals as prodrugs -- Nitrogen nucleophiles -- Beta-carotene and vision -- Prodrugs -- Sulfur nucleophiles -- Hydrogen nucleophiles -- Carbon nucleophiles -- Cyanohydrin derivatives in nature -- Baeyer-Villiger oxidation of aldehydes and ketones -- Spectroscopic analysis of aldehydes and ketones -- 21. Carboxylic acids and their derivatives -- Carboxylic acid derivatives -- Sedatives -- Preparation and reactions of acid chlorides -- Preparation and reactions of acid anhydrides -- Aspirin -- Esters -- Soap -- Esters as prodrugs -- Preparation and reactions amides -- Polyamides and polyesters -- Beta-lactam antibiotics -- Preparation and reactions of nitriles -- Spectroscopy of carboxylic acids and their derivatives -- 22. Alpha carbon chemistry: enols and enolates -- Alpha halogenation of enols and enolates -- Aldol reactions -- Muscle power -- Meat -- Claisen condensations -- Alkylation of the alpha position -- Conjugate addition reactions -- Glutathione conjugation and biological michael reactions -- 23. Amines -- Drug metabolism studies -- Fortunate side effects -- Amine ionization and drug distribution -- Preparation of amines via substitution reactions -- Preparation of amines via reductive amination -- Acylation of amines -- The Hofmann elimination -- Reactions of amines with nitrous acid -- Reactions of aryldiazonium ions -- Nitrogen heterocyles -- Cimetidine -- Spectroscopy of amines -- 24. Carbohydrates -- Classification of monosaccharides -- Configuration of aldoses -- Configuration of ketoses -- Diseases associated with insufficient glycoside formation -- Disaccharides -- Lactose intolerance -- Artificial sweeteners -- Polysaccharides -- Amino sugars -- N-glycosides -- Aminoglycoside antibiotics -- 25. Amino acids, peptides, and proteins -- Nutrition and sources of amino acids -- Forensic chemistry and fingerprint detection -- Polypeptide antibiotics -- Diseases caused by misfolded proteins -- Protein function -- 26. Lipids -- Waxes -- Triglycerides -- Soaps vs. synthetic detergents -- Phospholipids -- Selectivity of antifungal agents -- Steroids -- Cholesterol and heart disease -- Anabolic steroids and competitive sports -- Prostaglandins -- NSAIDs and COX-2 inhibitors -- Terpenes -- 27. Synthetic polymers -- Polymer classification Copolymers -- Safety glass and car windshields -- Polymer recycling.