[eBook] [PDF] for Organic Chemistry, 2nd Edition By David Klein

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Title Page Copyright Contents Preface 1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1.1 Introduction to Organic Chemistry 1.2 The Structural Theory of Matter 1.3 E... lectrons, Bonds, and Lewis Structures 1.4 Identifying Formal Charges 1.5 Induction and Polar Covalent Bonds PRACTICALLY SPEAKING: Electrostatic Potential Maps 1.6 Atomic Orbitals 1.7 Valence Bond Theory 1.8 Molecular Orbital Theory 1.9 Hybridized Atomic Orbitals 1.10 VSEPR Theory: Predicting Geometry 1.11 Dipole Moments and Molecular Polarity 1.12 Intermolecular Forces and Physical Properties PRACTICALLY SPEAKING: Biomimicry and Gecko Feet MEDICALLY SPEAKING: Drug-Receptor Interactions 1.13 Solubility MEDICALLY SPEAKING: Propofol: The Importance of Drug Solubility Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 2 Molecular Representations 2.1 Molecular Representations 2.2 Bond-Line Structures 2.3 Identifying Functional Groups MEDICALLY SPEAKING: Marine Natural Products 2.4 Carbon Atoms with Formal Charges 2.5 Identifying Lone Pairs 2.6 Three-Dimensional Bond-Line Structures MEDICALLY SPEAKING: Identifying the Pharmacophore 2.7 Introduction to Resonance 2.8 Curved Arrows 2.9 Formal Charges in Resonance Structures 2.10 Drawing Resonance Structures via Pattern Recognition 2.11 Assessing Relative Importance of Resonance Structures 2.12 Delocalized and Localized Lone Pairs Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 3 Acids and Bases 3.1 Introduction to Brønsted-Lowry Acids and Bases 3.2 Flow of Electron Density: Curved Arrow Notation MEDICALLY SPEAKING: Antacids and Heartburn 3.3 Brønsted-Lowry Acidity: A Quantitative Perspective MEDICALLY SPEAKING: Drug Distribution and pK[sub(a)] 3.4 Brønsted-Lowry Acidity: Qualitative Perspective 3.5 Position of Equilibrium and Choice of Reagents 3.6 Leveling Effect 3.7 Solvating Effects 3.8 Counterions PRACTICALLY SPEAKING: Baking Soda versus Baking Powder 3.9 Lewis Acids and Bases Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 4 Alkanes and Cycloalkanes 4.1 Introduction to Alkanes 4.2 Nomenclature of Alkanes PRACTICALLY SPEAKING: Pheromones: Chemical Messengers MEDICALLY SPEAKING: Naming Drugs 4.3 Constitutional Isomers of Alkanes 4.4 Relative Stability of Isomeric Alkanes 4.5 Sources and Uses of Alkanes PRACTICALLY SPEAKING: An Introduction to Polymers 4.6 Drawing Newman Projections 4.7 Conformational Analysis of Ethane and Propane 4.8 Conformational Analysis of Butane MEDICALLY SPEAKING: Drugs and Their Conformations 4.9 Cycloalkanes MEDICALLY SPEAKING: Cyclopropane as an Inhalation Anesthetic 4.10 Conformations of Cyclohexane 4.11 Drawing Chair Conformations 4.12 Monosubstituted Cyclohexane 4.13 Disubstituted Cyclohexane 4.14 Cis-trans Stereoisomerism 4.15 Polycyclic Systems Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 5 Stereoisomerism 5.1 Overview of Isomerism 5.2 Introduction to Stereoisomerism PRACTICALLY SPEAKING: The Sense of Smell 5.3 Designating Configuration Using the Cahn-Ingold-Prelog System MEDICALLY SPEAKING: Chiral Drugs 5.4 Optical Activity 5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 5.6 Symmetry and Chirality 5.7 Fischer Projections 5.8 Conformationally Mobile Systems 5.9 Resolution of Enantiomers Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 6 Chemical Reactivity and Mechanisms 6.1 Enthalpy 6.2 Entropy 6.3 Gibbs Free Energy PRACTICALLY SPEAKING: Explosives PRACTICALLY SPEAKING: Do Living Organisms Violate the Second Law of Thermodynamics? 6.4 Equilibria 6.5 Kinetics MEDICALLY SPEAKING: Nitroglycerin: An Explosive with Medicinal Properties PRACTICALLY SPEAKING: Beer-Making 6.6 Reading Energy Diagrams 6.7 Nucleophiles and Electrophiles 6.8 Mechanisms and Arrow Pushing 6.9 Combining the Patterns of Arrow Pushing 6.10 Drawing Curved Arrows 6.11 Carbocation Rearrangements 6.12 Reversible and Irreversible Reaction Arrows Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 7 Substitution Reactions 7.1 Introduction to Substitution Reactions 7.2 Alkyl Halides 7.3 Possible Mechanisms for Substitution Reactions 7.4 The S[sub(N)]2 Mechanism PRACTICALLY SPEAKING: S[sub(N)]2 Reactions in Biological Systems—Methylation 7.5 The S[sub(N)]1 Mechanism 7.6 Drawing the Complete Mechanism of an S[sub(N)]1 Reaction 7.7 Drawing the Complete Mechanism of an S[sub(N)]2 Reaction MEDICALLY SPEAKING: Radiolabelled Compounds in Diagnostic Medicine 7.8 Determining Which Mechanism Predominates 7.9 Selecting Reagents to Accomplish Functional Group Transformation MEDICALLY SPEAKING: Pharmacology and Drug Design Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 8 Alkenes: Structure and Preparation via Elimination Reactions 8.1 Introduction to Elimination Reactions 8.2 Alkenes in Nature and in Industry PRACTICALLY SPEAKING: Pheromones to Control Insect Populations 8.3 Nomenclature of Alkenes 8.4 Stereoisomerism in Alkenes MEDICALLY SPEAKING: Phototherapy Treatment for Neonatal Jaundice 8.5 Alkene Stability 8.6 Possible Mechanisms for Elimination 8.7 The E2 Mechanism 8.8 Drawing the Products of an E2 Reaction 8.9 The E1 Mechanism 8.10 Drawing the Complete Mechanism of an E1 Process 8.11 Drawing the Complete Mechanism of an E2 Process 8.12 Substitution vs. Elimination: Identifying the Reagent 8.13 Substitution vs. Elimination: Identifying the Mechanism(s) 8.14 Substitution vs. Elimination: Predicting the Products Review of Synthetically Useful Elimination Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 9 Addition Reactions of Alkenes 9.1 Introduction to Addition Reactions 9.2 Addition vs. Elimination: A Thermodynamic Perspective 9.3 Hydrohalogenation PRACTICALLY SPEAKING: Cationic Polymerization and Polystyrene 9.4 Acid-Catalyzed Hydration PRACTICALLY SPEAKING: Industrial Production of Ethanol 9.5 Oxymercuration-Demercuration 9.6 Hydroboration-Oxidation 9.7 Catalytic Hydrogenation PRACTICALLY SPEAKING: Partially Hydrogenated Fats and Oils 9.8 Halogenation and Halohydrin Formation 9.9 Anti Dihydroxylation 9.10 Syn Dihydroxylation 9.11 Oxidative Cleavage 9.12 Predicting Products of an Addition Reaction 9.13 Synthesis Strategies Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 10 Alkynes 10.1 Introduction to Alkynes MEDICALLY SPEAKING: The Role of Molecular Rigidity PRACTICALLY SPEAKING: Conducting Organic Polymers 10.2 Nomenclature of Alkynes 10.3 Acidity of Acetylene and Terminal Alkynes 10.4 Preparing Alkynes 10.5 Reduction of Alkynes 10.6 Hydrohalogenation of Alkynes 10.7 Hydration of Alkynes 10.8 Halogenation of Alkynes 10.9 Ozonolysis of Alkynes 10.10 Alkylation of Terminal Alkynes 10.11 Synthesis Strategies Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 11 Radical Reactions 11.1 Radicals 11.2 Common Patterns in Radical Mechanisms 11.3 Chlorination of Methane 11.4 Thermodynamic Considerations for Halogenation Reactions 11.5 Selectivity of Halogenation 11.6 Stereochemistry of Halogenation 11.7 Allylic Bromination 11.8 Atmospheric Chemistry and the Ozone Layer PRACTICALLY SPEAKING: Fighting Fires with Chemicals 11.9 Autooxidation and Antioxidants MEDICALLY SPEAKING: Why is an Overdose of Acetaminophen Fatal? 11.10 Radical Addition of HBr: Anti-Markovnikov Addition 11.11 Radical Polymerization 11.12 Radical Processes in the Petrochemical Industry 11.13 Halogenation as a Synthetic Technique Review of Synthetically Useful Radical Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 12 Synthesis 12.1 One-Step Syntheses 12.2 Functional Group Transformations 12.3 Reactions that Change the Carbon Skeleton MEDICALLY SPEAKING: Vitamins 12.4 How to Approach a Synthesis Problem MEDICALLY SPEAKING: The Total Synthesis of Vitamin B[sub(12)] 12.5 Retrosynthetic Analysis PRACTICALLY SPEAKING: Retrosynthetic Analysis 12.6 Practical Tips for Increasing Proficiency MEDICALLY SPEAKING: Total Synthesis of Taxol Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 13 Alcohols and Phenols 13.1 Structure and Properties of Alcohols MEDICALLY SPEAKING: Chain Length as a Factor in Drug Design 13.2 Acidity of Alcohols and Phenols 13.3 Preparation of Alcohols via Substitution or Addition 13.4 Preparation of Alcohols via Reduction 13.5 Preparation of Diols PRACTICALLY SPEAKING: Antifreeze 13.6 Preparation of Alcohols via Grignard Reagents 13.7 Protection of Alcohols 13.8 Preparation of Phenols MEDICALLY SPEAKING: Phenols as Antifungal Agents 13.9 Reactions of Alcohols: Substitution and Elimination PRACTICALLY SPEAKING: Drug Metabolism 13.10 Reactions of Alcohols: Oxidation PRACTICALLY SPEAKING: Breath Tests to Measure Blood Alcohol Level 13.11 Biological Redox Reactions PRACTICALLY SPEAKING: Biological Oxidation of Methanol and Ethanol 13.12 Oxidation of Phenol 13.13 Synthesis Strategies Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 14 Ethers and Epoxides; Thiols and Sulfides 14.1 Introduction to Ethers 14.2 Nomenclature of Ethers 14.3 Structure and Properties of Ethers MEDICALLY SPEAKING: Ethers as Inhalation Anesthetics 14.4 Crown Ethers MEDICALLY SPEAKING: Polyether Antibiotics 14.5 Preparation of Ethers 14.6 Reactions of Ethers 14.7 Nomenclature of Epoxides MEDICALLY SPEAKING: Epothilones as Novel Anticancer Agents 14.8 Preparation of Epoxides MEDICALLY SPEAKING: Active Metabolites and Drug Interactions 14.9 Enantioselective Epoxidation 14.10 Ring-Opening Reactions of Epoxides PRACTICALLY SPEAKING: Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment MEDICALLY SPEAKING: Cigarette Smoke and Carcinogenic Epoxides 14.11 Thiols and Sulfides 14.12 Synthesis Strategies Involving Epoxides Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 15 Infrared Spectroscopy and Mass Spectrometry 15.1 Introduction to Spectroscopy PRACTICALLY SPEAKING: Microwave Ovens 15.2 IR Spectroscopy MEDICALLY SPEAKING: IR Thermal Imaging for Cancer Detection 15.3 Signal Characteristics: Wavenumber 15.4 Signal Characteristics: Intensity PRACTICALLY SPEAKING: IR Spectroscopy for Testing Blood Alcohol Levels 15.5 Signal Characteristics: Shape 15.6 Analyzing an IR Spectrum 15.7 Using IR Spectroscopy to Distinguish between Two Compounds 15.8 Introduction to Mass Spectrometry PRACTICALLY SPEAKING: Mass Spectrometry for Detecting Explosives 15.9 Analyzing the (M)[sup(+•)] Peak 15.10 Analyzing the (M+1)[sup(+•)] Peak 15.11 Analyzing the (M+2)[sup(+•)] Peak 15.12 Analyzing the Fragments 15.13 High Resolution Mass Spectrometry 15.14 Gas Chromatography—Mass Spectrometry 15.15 Mass Spectrometry of Large Biomolecules MEDICALLY SPEAKING: Medical Applications of Mass Spectrometry 15.16 Hydrogen Deficiency Index: Degrees of Unsaturation Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 16 Nuclear Magnetic Resonance Spectroscopy 16.1 Introduction to NMR Spectroscopy 16.2 Acquiring a [sup(1)]H NMR Spectrum 16.3 Characteristics of a [sup(1)]H NMR Spectrum 16.4 Number of Signals 16.5 Chemical Shift 16.6 Integration 16.7 Multiplicity 16.8 Drawing the Expected [sup(1)]H NMR Spectrum of a Compound 16.9 Using [sup(1)]H NMR Spectroscopy to Distinguish between Compounds MEDICALLY SPEAKING: Detection of Impurities in Heparin Sodium Using [sup(1)]H NMR Spectroscopy 16.10 Analyzing a [sup(1)]H NMR Spectrum 16.11 Acquiring a [sup(13)]C NMR Spectrum 16.12 Chemical Shifts in [sup(13)]C NMR Spectroscopy 16.13 DEPT [sup(13)]C NMR Spectroscopy MEDICALLY SPEAKING: Magnetic Resonance Imaging (MRI) Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 17 Conjugated Pi Systems and Pericyclic Reactions 17.1 Classes of Dienes 17.2 Conjugated Dienes 17.3 Molecular Orbital Theory 17.4 Electrophilic Addition 17.5 Thermodynamic Control vs. Kinetic Control PRACTICALLY SPEAKING: Natural and Synthetic Rubbers 17.6 An Introduction to Pericyclic Reactions 17.7 Diels–Alder Reactions 17.8 MO Description of Cycloadditions 17.9 Electrocyclic Reactions 17.10 Sigmatropic Rearrangements MEDICALLY SPEAKING: The Photoinduced Biosynthesis of Vitamin D 17.11 UV-VIS Spectroscopy PRACTICALLY SPEAKING: Sunscreens 17.12 Color PRACTICALLY SPEAKING: Bleach 17.13 The Chemistry of Vision Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 18 Aromatic Compounds 18.1 Introduction to Aromatic Compounds PRACTICALLY SPEAKING: What Is Coal? 18.2 Nomenclature of Benzene Derivatives 18.3 Structure of Benzene 18.4 Stability of Benzene PRACTICALLY SPEAKING: Molecular Cages 18.5 Aromatic Compounds Other than Benzene MEDICALLY SPEAKING: The Development of Nonsedating Antihistamines 18.6 Reactions at the Benzylic Position 18.7 Reduction of the Aromatic Moiety 18.8 Spectroscopy of Aromatic Compounds PRACTICALLY SPEAKING: Buckyballs and Nanotubes Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 19 Aromatic Substitution Reactions 19.1 Introduction to Electrophilic Aromatic Substitution 19.2 Halogenation MEDICALLY SPEAKING: Halogenation Drug Design 19.3 Sulfonation PRACTICALLY SPEAKING: What Are Those Colors Fruity Pebbles? 19.4 Nitration 19.5 Friedel–Crafts Alkylation MEDICALLY SPEAKING: The Discovery of Prodrugs 19.6 Friedel–Crafts Acylation 19.7 Activating Groups 19.8 Deactivating Groups 19.9 Halogens: The Exception 19.10 Determining the Directing Effects of a Substituent 19.11 Multiple Substituents 19.12 Synthesis Strategies 19.13 Nucleophilic Aromatic Substitution 19.14 Elimination-Addition 19.15 Identifying the Mechanism of an Aromatic Substitution Reaction Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 20 Aldehydes and Ketones 20.1 Introduction to Aldehydes and Ketones 20.2 Nomenclature 20.3 Preparing Aldehydes and Ketones: A Review 20.4 Introduction to Nucleophilic Addition Reactions 20.5 Oxygen Nucleophiles MEDICALLY SPEAKING: Acetals as Prodrugs 20.6 Nitrogen Nucleophiles PRACTICALLY SPEAKING: Beta-Carotene Vision 20.7 Hydrolysis of Acetals, Imines, and Enamines MEDICALLY SPEAKING: Prodrugs 20.8 Sulfur Nucleophiles 20.9 Hydrogen Nucleophiles 20.10 Carbon Nucleophiles PRACTICALLY SPEAKING: Cyanohydrin Derivatives in Nature 20.11 Baeyer-Villiger Oxidation of Aldehydes and Ketones 20.12 Synthesis Strategies 20.13 Spectroscopic Analysis of Aldehydes and Ketones Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 21 Carboxylic Acids and Their Derivatives 21.1 Introduction to Carboxylic Acids 21.2 Nomenclature of Carboxylic Acids 21.3 Structure and Properties of Carboxylic Acids 21.4 Preparation of Carboxylic Acids 21.5 Reactions of Carboxylic Acids 21.6 Introduction to Carboxylic Acid Derivatives MEDICALLY SPEAKING: Sedatives 21.7 Reactivity of Carboxylic Acid Derivatives 21.8 Preparation and Reactions of Acid Chlorides 21.9 Preparation and Reactions of Acid Anhydrides MEDICALLY SPEAKING: How does Aspirin Work? 21.10 Preparation of Esters 21.11 Reactions of Esters PRACTICALLY SPEAKING: How Soap Is Made MEDICALLY SPEAKING: Esters as Prodrugs 21.12 Preparation and Reactions of Amides PRACTICALLY SPEAKING: Polyamides and Polyesters MEDICALLY SPEAKING: Beta-Lactam Antibiotics 21.13 Preparation and Reactions of Nitriles 21.14 Synthesis Strategies 21.15 Spectroscopy of Carboxylic Acids and Their Derivatives Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 22 Alpha Carbon Chemistry: Enols and Enolates 22.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 22.2 Alpha Halogenation of Enols and Enolates 22.3 Aldol Reactions PRACTICALLY SPEAKING: Muscle Power PRACTICALLY SPEAKING: Why Meat from Younger Animals is Softer 22.4 Claisen Condensations 22.5 Alkylation of the Alpha Position 22.6 Conjugate Addition Reactions MEDICALLY SPEAKING: Glutathione Conjugation and Biological Michael Reactions 22.7 Synthesis Strategies Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 23 Amines 23.1 Introduction to Amines MEDICALLY SPEAKING: Drug Metabolism Studies 23.2 Nomenclature of Amines 23.3 Properties of Amines MEDICALLY SPEAKING: Fortunate Side Effects MEDICALLY SPEAKING: Amine Ionization and Drug Distribution 23.4 Preparation of Amines: A Review 23.5 Preparation of Amines via Substitution Reactions 23.6 Preparation of Amines via Reductive Amination 23.7 Synthesis Strategies 23.8 Acylation of Amines 23.9 The Hofmann Elimination 23.10 Reactions of Amines with Nitrous Acid 23.11 Reactions of Aryldiazonium Ions 23.12 Nitrogen Heterocycles MEDICALLY SPEAKING: H[sub(2)]-Receptor Antagonists and the Development of Cimetidine 23.13 Spectroscopy of Amines Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 24 Carbohydrates 24.1 Introduction to Carbohydrates 24.2 Classifying Monosaccharides 24.3 Configuration of Aldoses 24.4 Configuration of Ketoses 24.5 Cyclic Structures of Monosaccharides 24.6 Reactions of Monosaccharides 24.7 Disaccharides MEDICALLY SPEAKING: Lactose Intolerance PRACTICALLY SPEAKING: Artificial Sweeteners 24.8 Polysaccharides 24.9 Amino Sugars 24.10 N-Glycosides MEDICALLY SPEAKING: Aminoglycoside Antibiotics MEDICALLY SPEAKING: Erythromycin Biosynthesis Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 25 Amino Acids, Peptides, and Proteins 25.1 Introduction to Amino Acids, Peptides, and Proteins 25.2 Structure and Properties of Amino Acids PRACTICALLY SPEAKING: Nutrition and Sources of Amino Acids PRACTICALLY SPEAKING: Forensic Chemistry and Fingerprint Detection 25.3 Amino Acid Synthesis 25.4 Structure of Peptides MEDICALLY SPEAKING: Polypeptide Antibiotics 25.5 Sequencing a Peptide 25.6 Peptide Synthesis 25.7 Protein Structure MEDICALLY SPEAKING: Diseases Caused by Misfolded Proteins 25.8 Protein Function Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 26 Lipids 26.1 Introduction to Lipids 26.2 Waxes 26.3 Triglycerides 26.4 Reactions of Triglycerides PRACTICALLY SPEAKING: Soaps vs. Synthetic Detergents 26.5 Phospholipids MEDICALLY SPEAKING: Selectivity of Antifungal Agents 26.6 Steroids MEDICALLY SPEAKING: Cholesterol and Heart Disease MEDICALLY SPEAKING: Anabolic Steroids and Competitive Sports 26.7 Prostaglandins MEDICALLY SPEAKING: NSAIDs and COX-2 Inhibitors 26.8 Terpenes Review of Synthetically Useful Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 27 Synthetic Polymers 27.1 Introduction to Synthetic Polymers 27.2 Nomenclature of Synthetic Polymers 27.3 Copolymers 27.4 Polymer Classification by Reaction Type 27.5 Polymer Classification by Mode of Assembly 27.6 Polymer Classification by Structure 27.7 Polymer Classification by Properties PRACTICALLY SPEAKING: Safety Glass and Car Windshields 27.8 Polymer Recycling Review of Reactions Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems Appendix A: Nomenclature of Polyfunctional Compounds Glossary Credits Index EULA [Show More]

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