[eBook] [PDF] for Organic Chemistry 3rd Edition By by David R. Klein

Document Content and Description Below

Cover Approximate pKa Values for Commonly Encountered Structural Types Title Page Preface 1 A Review of General Chemistry 1.1 Introduction to Organic Chemistry 1.2 The Structural Theory of Matte... r 1.3 Electrons, Bonds, and Lewis Structures 1.4 Identifying Formal Charges 1.5 Induction and Polar Covalent Bonds 1.6 Atomic Orbitals 1.7 Valence Bond Theory 1.8 Molecular Orbital Theory 1.9 Hybridized Atomic Orbitals 1.10 Predicting Molecular Geometry: VSEPR Theory 1.11 Dipole Moments and Molecular Polarity 1.12 Intermolecular Forces and Physical Properties 1.13 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 2.4 Carbon Atoms with Formal Charges 2.5 Identifying Lone Pairs 2.6 Three-Dimensional Bond-Line Structures 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 the Relative Importance of Resonance Structures 2.12 The Resonance Hybrid 2.13 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 3.3 Brønsted-Lowry Acidity: Quantitative Perspective 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 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 4.3 Constitutional Isomers of Alkanes 4.4 Relative Stability of Isomeric Alkanes 4.5 Sources and Uses of Alkanes 4.6 Drawing Newman Projections 4.7 Conformational Analysis of Ethane and Propane 4.8 Conformational Analysis of Butane 4.9 Cycloalkanes 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 5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 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 Chiral Compounds That Lack a Chiral Center 5.10 Resolution of Enantiomers 5.11 E and Z Designations for Diastereomeric Alkenes 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 6.4 Equilibria 6.5 Kinetics 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 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 7.1 Introduction to Substitution and Elimination Reactions 7.2 Nomenclature and Uses of Alkyl Halides 7.3 SN2 Reactions 7.4 Nucleophilic Strength and Solvent Effects in SN2 Reactions 7.5 SN2 Reactions in Biological Systems—Methylation 7.6 Introduction to E2 Reactions 7.7 Nomenclature and Stability of Alkenes 7.8 Regiochemical and Stereochemical Outcomes for E2 Reactions 7.9 Unimolecular Reactions (SN1 and E1) 7.10 Kinetic Isotope Effects in Elimination Reactions 7.11 Predicting Products: Substitution vs. Elimination 7.12 Substitution and Elimination Reactions with Other Substrates 7.13 Synthesis Strategies Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 8 Addition Reactions of Alkenes 8.1 Introduction to Addition Reactions 8.2 Alkenes in Nature and in Industry 8.3 Addition vs. Elimination: A Thermodynamic Perspective 8.4 Hydrohalogenation 8.5 Acid-Catalyzed Hydration 8.6 Oxymercuration-Demercuration 8.7 Hydroboration-Oxidation 8.8 Catalytic Hydrogenation 8.9 Halogenation and Halohydrin Formation 8.10 Anti Dihydroxylation 8.11 Syn Dihydroxylation 8.12 Oxidative Cleavage 8.13 Predicting the Products of an Addition Reaction 8.14 Synthesis Strategies Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 9 Alkynes 9.1 Introduction to Alkynes 9.2 Nomenclature of Alkynes 9.3 Acidity of Acetylene and Terminal Alkynes 9.4 Preparation of Alkynes 9.5 Reduction of Alkynes 9.6 Hydrohalogenation of Alkynes 9.7 Hydration of Alkynes 9.8 Halogenation of Alkynes 9.9 Ozonolysis of Alkynes 9.10 Alkylation of Terminal Alkynes 9.11 Synthesis Strategies Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 10 Radical Reactions 10.1 Radicals 10.2 Common Patterns in Radical Mechanisms 10.3 Chlorination of Methane 10.4 Thermodynamic Considerations for Halogenation Reactions 10.5 Selectivity of Halogenation 10.6 Stereochemistry of Halogenation 10.7 Allylic Bromination 10.8 Atmospheric Chemistry and the Ozone Layer 10.9 Autooxidation and Antioxidants 10.10 Radical Addition of HBr: Anti-Markovnikov Addition 10.11 Radical Polymerization 10.12 Radical Processes in the Petrochemical Industry 10.13 Halogenation as a Synthetic Technique Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 11 Synthesis 11.1 One-Step Syntheses 11.2 Functional Group Transformations 11.3 Reactions That Change the Carbon Skeleton 11.4 How to Approach a Synthesis Problem 11.5 Retrosynthetic Analysis 11.6 Green Chemistry 11.7 Practical Tips for Increasing Proficiency Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 12 Alcohols and Phenols 12.1 Structure and Properties of Alcohols 12.2 Acidity of Alcohols and Phenols 12.3 Preparation of Alcohols via Substitution or Addition 12.4 Preparation of Alcohols via Reduction 12.5 Preparation of Diols 12.6 Preparation of Alcohols via Grignard Reagents 12.7 Protection of Alcohols 12.8 Preparation of Phenols 12.9 Reactions of Alcohols: Substitution and Elimination 12.10 Reactions of Alcohols: Oxidation 12.11 Biological Redox Reactions 12.12 Oxidation of Phenol 12.13 Synthesis Strategies Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 13 Ethers and Epoxides; Thiols and Sulfides 13.1 Introduction to Ethers 13.2 Nomenclature of Ethers 13.3 Structure and Properties of Ethers 13.4 Crown Ethers 13.5 Preparation of Ethers 13.6 Reactions of Ethers 13.7 Nomenclature of Epoxides 13.8 Preparation of Epoxides 13.9 Enantioselective Epoxidation 13.10 Ring-Opening Reactions of Epoxides 13.11 Thiols and Sulfides 13.12 Synthesis Strategies Involving Epoxides Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 14 Infrared Spectroscopy and Mass Spectrometry 14.1 Introduction to Spectroscopy 14.2 IR Spectroscopy 14.3 Signal Characteristics: Wavenumber 14.4 Signal Characteristics: Intensity 14.5 Signal Characteristics: Shape 14.6 Analyzing an IR Spectrum 14.7 Using IR Spectroscopy to Distinguish between Two Compounds 14.8 Introduction to Mass Spectrometry 14.9 Analyzing the (M) Peak 14.10 Analyzing the (M+1) Peak 14.11 Analyzing the (M+2) Peak 14.12 Analyzing the Fragments 14.13 High-Resolution Mass Spectrometry 14.14 Gas Chromatography–Mass Spectrometry 14.15 Mass Spectrometry of Large Biomolecules 14.16 Hydrogen Deficiency Index: Degrees of Unsaturation Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 15 Nuclear Magnetic Resonance Spectroscopy 15.1 Introduction to NMR Spectroscopy 15.2 Acquiring a H NMR Spectrum 15.3 Characteristics of a H NMR Spectrum 15.4 Number of Signals 15.5 Chemical Shift 15.6 Integration 15.7 Multiplicity 15.8 Drawing the Expected H NMR Spectrum of a Compound 15.9 Using H NMR Spectroscopy to Distinguish between Compounds 15.10 Analyzing a H NMR Spectrum 15.11 Acquiring a C NMR Spectrum 15.12 Chemical Shifts in C NMR Spectroscopy 15.13 DEPT C NMR Spectroscopy Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 16 Conjugated Pi Systems and Pericyclic Reactions 16.1 Classes of Dienes 16.2 Conjugated Dienes 16.3 Molecular Orbital Theory 16.4 Electrophilic Addition 16.5 Thermodynamic Control vs. Kinetic Control 16.6 An Introduction to Pericyclic Reactions 16.7 Diels–Alder Reactions 16.8 MO Description of Cycloadditions 16.9 Electrocyclic Reactions 16.10 Sigmatropic Rearrangements 16.11 UV-Vis Spectroscopy 16.12 Color 16.13 Chemistry of Vision Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 17 Aromatic Compounds 17.1 Introduction to Aromatic Compounds 17.2 Nomenclature of Benzene Derivatives 17.3 Structure of Benzene 17.4 Stability of Benzene 17.5 Aromatic Compounds Other Than Benzene 17.6 Reactions at the Benzylic Position 17.7 Reduction of Benzene and Its Derivatives 17.8 Spectroscopy of Aromatic Compounds Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 18 Aromatic Substitution Reactions 18.1 Introduction to Electrophilic Aromatic Substitution 18.2 Halogenation 18.3 Sulfonation 18.4 Nitration 18.5 Friedel–Crafts Alkylation 18.6 Friedel–Crafts Acylation 18.7 Activating Groups 18.8 Deactivating Groups 18.9 Halogens: The Exception 18.10 Determining the Directing Effects of a Substituent 18.11 Multiple Substituents 18.12 Synthesis Strategies 18.13 Nucleophilic Aromatic Substitution 18.14 Elimination-Addition 18.15 Identifying the Mechanism of an Aromatic Substitution Reaction Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 19 Aldehydes and Ketones 19.1 Introduction to Aldehydes and Ketones 19.2 Nomenclature 19.3 Preparing Aldehydes and Ketones: A Review 19.4 Introduction to Nucleophilic Addition Reactions 19.5 Oxygen Nucleophiles 19.6 Nitrogen Nucleophiles 19.7 Hydrolysis of Acetals, Imines, and Enamines 19.8 Sulfur Nucleophiles 19.9 Hydrogen Nucleophiles 19.10 Carbon Nucleophiles 19.11 Baeyer–Villiger Oxidation of Aldehydes and Ketones 19.12 Synthesis Strategies 19.13 Spectroscopic Analysis of Aldehydes and Ketones Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 20 Carboxylic Acids and Their Derivatives 20.1 Introduction to Carboxylic Acids 20.2 Nomenclature of Carboxylic Acids 20.3 Structure and Properties of Carboxylic Acids 20.4 Preparation of Carboxylic Acids 20.5 Reactions of Carboxylic Acids 20.6 Introduction to Carboxylic Acid Derivatives 20.7 Reactivity of Carboxylic Acid Derivatives 20.8 Preparation and Reactions of Acid Chlorides 20.9 Preparation and Reactions of Acid Anhydrides 20.10 Preparation of Esters 20.11 Reactions of Esters 20.12 Preparation and Reactions of Amides 20.13 Preparation and Reactions of Nitriles 20.14 Synthesis Strategies 20.15 Spectroscopy of Carboxylic Acids and Their Derivatives Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 21 Alpha Carbon Chemistry: Enols and Enolates 21.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 21.2 Alpha Halogenation of Enols and Enolates 21.3 Aldol Reactions 21.4 Claisen Condensations 21.5 Alkylation of the Alpha Position 21.6 Conjugate Addition Reactions 21.7 Synthesis Strategies Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 22 Amines 22.1 Introduction to Amines 22.2 Nomenclature of Amines 22.3 Properties of Amines 22.4 Preparation of Amines: A Review 22.5 Preparation of Amines via Substitution Reactions 22.6 Preparation of Amines via Reductive Amination 22.7 Synthesis Strategies 22.8 Acylation of Amines 22.9 Hofmann Elimination 22.10 Reactions of Amines with Nitrous Acid 22.11 Reactions of Aryl Diazonium Ions 22.12 Nitrogen Heterocycles 22.13 Spectroscopy of Amines Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 23 Introduction to Organometallic Compounds 23.1 General Properties of Organometallic Compounds 23.2 Organolithium and Organomagnesium Compounds 23.3 Lithium Dialkyl Cuprates (Gilman Reagents) 23.4 The Simmons–Smith Reaction and Carbenoids 23.5 Stille Coupling 23.6 Suzuki Coupling 23.7 Negishi Coupling 23.8 The Heck Reaction 23.9 Alkene Metathesis Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems 24 Carbohydrates 24.1 Introduction to Carbohydrates 24.2 Classification of 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 24.8 Polysaccharides 24.9 Amino Sugars 24.10 N-Glycosides 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 25.3 Amino Acid Synthesis 25.4 Structure of Peptides 25.5 Sequencing a Peptide 25.6 Peptide Synthesis 25.7 Protein Structure 25.8 Protein Function 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 26.5 Phospholipids 26.6 Steroids 26.7 Prostaglandins 26.8 Terpenes 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 27.8 Polymer Recycling Review of Concepts & Vocabulary SkillBuilder Review Practice Problems Integrated Problems Challenge Problems Student Study Guide and Solutions Manual Title Page Chapter 1 A Review of General Chemistry: Electrons, Bonds and Molecular Properties Chapter 2 Molecular Representations Chapter 3 Acids and Bases Chapter 4 Alkanes and Cycloalkanes Chapter 5 Stereoisomerism Chapter 6 Chemical Reactivity and Mechanisms Chapter 7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions Chapter 8 Addition Reactions of Alkenes Chapter 9 Alkynes Chapter 10 Radical Reactions Chapter 11 Synthesis Chapter 12 Alcohols Chapter 13 Ethers and Epoxides; Thiols and Sulfides Chapter 14 Infrared Spectroscopy and Mass Spectrometry Chapter 15 Nuclear Magnetic Resonance Spectroscopy Chapter 16 Conjugated Pi Systems and Pericyclic Reactions Chapter 17 Aromatic Compounds Chapter 18 Aromatic Substitution Reactions Chapter 19 Ketones and Aldehydes Chapter 20 Carboxylic Acids and Their Derivatives Chapter 21 Alpha Carbon Chemistry: Enols and Enolates Chapter 22 Amines Chapter 23 Organometallic Compounds Chapter 24 Carbohydrates Chapter 25 Amino Acids, Peptides, and Proteins Chapter 26 Lipids Chapter 27 Synthetic Polymers Appendix Nomenclature of Polyfunctional Compounds Appendix Nomenclature of Polyfunctional Compounds Glossary Credits Index Examples of Common Functional Groups Periodic Table of Elements End User License Agreement Read More [Show More]

Last updated: 1 year ago

Preview 1 out of 1344 pages