Organic Chemistry

An Acid-Base Approach, Third Edition

Häftad, Engelska, 2024

Av Michael B. Smith, USA) Smith, Michael B. (University of Connecticut, Storrs

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Based on the premise that many, if not most, reactions in organic chemistry can be explained by variations of fundamental acid–base concepts, Organic Chemistry: An Acid–Base Approach provides a framework for understanding the subject that goes beyond mere memorization. Using several techniques to develop a relational understanding, it helps students fully grasp the essential concepts at the root of organic chemistry.This new edition was rewritten largely with the feedback of students in mind and is also based on the author’s classroom experiences using the previous editions.Highlights of the Third Edition Include:Extensively revised chapters that improve the presentation of material. Features the contributions of more than 65 scientists, highlighting the diversity in organic chemistry. Features the current work of over 30 organic chemists, highlighting the diversity in organic chemistry. Many new reactions are featured that are important in modern organic chemistry. Video lectures are provided in a .mov format, accessible online as a ‘built-in’ ancillary for the book. Instructor and Student Resources —includes scientist images and solutions manual for instructors. The third edition of Organic Chemistry: An Acid–Base Approach constitutes a significant improvement upon a unique introductory technique to organic chemistry. The reactions and mechanisms it covers are the most fundamental concepts in organic chemistry that are applied to industry, biological chemistry, biochemistry, molecular biology, and pharmacy. Using an illustrated conceptual approach rather than presenting sets of principles and theories to memorize, it gives students a more concrete understanding of the material.

Produktinformation

Utgivningsdatum2024-10-09
Mått210 x 280 x 39 mm
Vikt2 200 g
FormatHäftad
SpråkEngelska
Antal sidor694
Upplaga3
FörlagTaylor & Francis Ltd
ISBN9781032006161

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Professor Michael B. Smith was born in Detroit, Michigan in 1946 and moved to Madison Heights, Virginia in 1957, where he attended high school at Amherst County High School. He received an A.A. from Ferrum College in 1967 and a B.S. in chemistry from Virginia Polytechnic Institute in 1969. After working for three years at the Newport News Shipbuilding and Dry Dock Co. in Newport News VA as an analytical chemist, he entered graduate school at Purdue University. He received a Ph.D. in Organic chemistry in 1977, under the auspices of Professor Joe Wolinsky. Professor Smith spent one year as a faculty research associate at the Arizona State University with Professor G. Robert Pettit, working on the isolation of cytotoxic principles from plants and sponges. He spent a second year of postdoctoral work with Professor Sidney M. Hecht at the Massachusetts Institute of Technology, working on the synthesis of bleomycin A2.Professor Smith began his academic career at the University of Connecticut in 1979, where he achieved the rank of professor of chemistry. In 1986 he spent a sabbatical leave in the laboratories of Professor Leon Ghosez, at the Université Catholique de Louvain in Louvain-la-Neuve, Belgium, as a visiting professor. He retired as a full professor from the University of Connecticut on January 1, 2017, and is currently pursuing his interests as an author.

Chapter 1: Introduction 1.1. A Brief History of Organic Chemistry 1.2. The Variety and Beauty of Organic Molecules Chapter 2: Why Is an Acid-Base Theme Important? 2.1. Traditional Acid and Base Theory 2.2. There are Two Acid-Base Definitions: How Are They Related? 2.3. Acid-Base Equilibria and Equilibrium Constants 2.4. Electronegativity and Atom Size 2.4.A. Electronegativity 2.4. B. Atom Size 2.5. Atom Size and Electronegativity Arguments Applied to Acids and Bases 2.6. Resonance, Electron Dispersion and Base Strength 2.7. Lewis Acids and Bases 2.8. Why Is Acid–Base Chemistry a Theme for Organic Chemistry? 2.9. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 3: Bonding 3.1. Atomic orbitals and Electrons 3.1.A. Atomic Orbitals 3.1.B. Electronic Configuration 3.2. Ionic versus Covalent Chemical Bonds 3.3. Covalent Bonds 3.4. Linear Combination of Atomic Orbital (LCAO) Model 3.5. Tetrahedral Carbons and sp3 Hybridization 3.5.A. The Experimentally Determined Structure of Methane 3.5.B. Electron Promotion and sp3 Hybridization 3.5.C. The Hybrid Carbon Model of sp3-Hybrid Orbitals 3.6. The Valence Shell Electron Pair Repulsion (VSEPR) Model 3.7. Breaking Covalent Bonds 3.8. Carbon Bonded to Heteroatoms 3.8.A. A Covalent Bond Between Carbon and a Heteroatom: Bond Polarization 3.8.B. Bond Polarity, Bond Moments, and Bond Strength Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 4: Alkanes, Isomers, and an Introduction to Nomenclature 4.1. Alkanes 4.2. Structural Variations of Alkane Hydrocarbons 4.2.A. Straight-chain and Branched Alkanes 4.2.B. Isomers 4.3. The IUPAC Rules of Nomenclature 4.3.A. Prefixes and Simple Alkanes 4.3.B. Common Names 4.3.C. Halogens are Substituents 4.3.D. Multiple Substituents 4.3.E. Complex Substituents 4.4. Rings Made of Carbon: Cyclic Compounds 4.5. The Acid or Base Properties of Alkanes 4.6. Combustion Analysis and Empirical Formulas 4.7. Commercial and Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 5: Functional Groups 5.1. -Bonds. The C=C Unit and Alkenes 5.2. -Bonds. The CºC Unit and Alkynes 5.3. Hydrocarbons With Several -Bonds 5.4. Terpenes 5.5. Heteroatom Functional Groups 5.5.A. Alcohols and Thiols 5.5.B. Ethers and Dithioethers (Sulfides) 5.5.C. Amines 5.6. Functional Groups With Polarized -Bonds 5.6.A. The Carbonyl Functional Group, C=O 5.6.B. Ketones and Aldehydes 5.6.C. Carboxylic Acids, Carboxylic Anions and Resonance 5.6.D. Double and Triple Bonds to Nitrogen 5.7. Acid-Base Properties of Functional Groups 5.8. Physical Properties and Intermolecular Forces 5.8.A. Boiling Point 5.8.B. Solubility 5.8.C. Melting Point 5.9. Benzene: A Special Cyclic Hydrocarbon 5.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 6: Acids, Bases, and Nucleophiles 6.1. Acid-Base Equilibria 6.2. Carboxylic Acids and Sulfonic Acids 6.2.A. Carboxylic Acids 6.2.B Sulfonic Acids 6.3. Factors That Influence the Strength of a Carboxylic Acid 6.3.A. Stability of the Conjugate Base 6.3.B. Inductive Effects 6.3.C. Solvent Effects 6.4. Alcohols Are Amphoteric 6.5. Amines 6.6. Carbon Acids 6.6.A. Terminal Alkynes Are Weak Acids 6.6.B. -Hydrogen Atoms and Carbonyls 6.7. Organic Bases 6.7.A. Amines 6.7.B. Alcohols Are Bases 6.7.C. Ethers Are Bases 6.7.D. Carbonyl Compounds Are Bases 6.7.E. Alkenes and Alkynes Are Bases 6.8. Lewis Acids and Bases 6.9. Nucleophiles 6.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 7. Chemical Reactions, Bond Energy, and Kinetics 7.1. A Chemical Reaction 7.2. Reactive Intermediates 7.2.A. Carbocations (Carbenium ions) 7.2.B. Carbanions 7.2.C. Radicals 7.3 Formal Charge 7.4. Free Energy: Enthalpy and Entropy 7.5. Bond Dissociation Enthalpy and Reactions 7.6. Transition States 7.7. Competing Reactions 7.8. Reversible Chemical Reactions 7.9. Reaction Curves and Intermediates 7.10. Mechanisms 7.11. Kinetics 7.11.A. Reaction Rate and First-Order Reactions 7.11.B. Second-Order Reactions 7.11.C. Half Life 7.11.D. No Reaction 7.12. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 8: Conformations 8.1. Rotation Around C—C Bonds 8.1.A. Staggered and Eclipsed Rotamers 8.1.B. Torsional Strain: Steric Hindrance and Energy Barriers 8.2. Longer Chain Alkanes 8.3. Influence of Heteroatoms on the Rotamer Population 8.3.A. Halogen Substituents 8.3.B. OH or NH Groups in Alcohols or Amines 8.4. Introducing -Bonds 8.5. Cyclic Alkanes 8.5.A. Strain and Steric Hindrance in Cyclic Alkanes 8.5.B. Conformations of C3–C5 Cycloalkanes 8.5.C. Conformationally Mobile Cyclohexane 8.6. Substituted Cyclohexanes. A1,3-Strain 8.7. Large Rings 8.8 Cyclic Alkenes 8.9. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 9: Stereoisomers: Chirality, Enantiomers, and Diastereomers 9.1. Stereogenic Carbons and Stereoisomers 9.2. Absolute Configuration [(R) and (S) Nomenclature] 9.3. Specific Rotation: A Physical Property 9.4. Circular Dichroism 9.5. Diastereomers 9.6. Alkenes 9.7. Cis and Trans Substituents Attached to Rings 9.8. Stereogenic Centers in Cyclic Molecules 9.9. Stereogenic Centers in Bicyclic Molecules 9.10. Optical Resolution 9.11. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 10: Acid–Base Reactions of -Bonds: Addition Reactions 10.1. Carbocation Stability 10.2. Alkenes React With Brønsted-Lowry Acids 10.3. Carbocation Rearrangements 10.4. Hydration Reactions of Alkenes 10.5. Alkenes React With Dihalogens 10.5.A Dihalogenation 10.5.B. Diastereoselectivity in the Dihalogenation Reaction of Alkenes 10.5.C. Reaction With Aqueous Solutions of Halogens (Hypohalous Acids) 10.6. Alkenes React With Borane 10.7. Alkenes React With Mercury(II) Compounds 10.8. Alkynes React as Bases 10.8.A. Reaction With Brønsted-Lowry Acids 10.8.B. Hydration of Alkynes 10.8.C. Dihalogenation of Alkynes 10.8.D. Hydroboration of Alkynes 10.8.E. Oxymercuration of Alkynes 10.9. Metathesis 10.10. Non-Ionic Reactions: Radical Reactions 10.11. Polymerization 10.12. Organization of Reaction Types 10.13. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 11: Substitution Reactions 11.1. Alkyl Halides, Sulfonate Esters, and the Electrophilic C—X Bond 11.2. The SN2 Reaction 11.2.A. Nucleophilic Approach to an Electrophilic Carbon 11.2.B. Reaction Rate and Energy Requirements 11.2.C. The Role of the Solvent 11.3. Functional Group Transformations Via the SN2 Reaction 11.4. The SN1 Reaction 11.5. Substitution Reactions of Alcohols 11.5.A. Alcohols React With Mineral Acids 11.5.B. Sulfur and Phosphorous Halide Reagents 11.5.C. Mitsunobu Reaction 11.6. Reactions of Ethers 11.6.A. Ethers React as Brønsted–Lowry Bases 11.6.B. Reactions of Epoxides 11.7. Free Radical Halogenation of Alkanes 11.8. C—H Substitution 11.9. Organization of Reaction Types 11.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 12: Elimination and p-Bond-Forming Reactions 12.1. Bimolecular Elimination 12.2. Stereochemical Consequences of the E2 Reaction 12.3. The E2 Reaction in Cyclic Molecules 12.4. Unimolecular Elimination: The E1 Reaction 12.5. Intramolecular Elimination 12.6. Elimination Reactions of Vinyl Halides: Formation of Alkynes 12.7. Substitution versus Elimination 12.8. Strength and Limitations of the Simplifying Assumptions 12.9. Organization of Reaction Types 12.10. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK 13: Spectroscopic Methods of Identification 13.1. Light and Energy 13.2. Mass Spectrometry 13.3. Infrared Spectroscopy 13.3.A. Absorbing Infrared Light and the Infrared Spectrophotometer 13.3.B. The Infrared Spectrum and Functional Group Absorptions 13.4. Nuclear Magnetic Resonance Spectroscopy 13.4.A. The Nuclear Magnetic Resonance Experiment 13.4.B. The Proton NMR Spectrum 13.5. Identifying Monofunctional Molecules 13.6. Carbon-13 NMR Spectroscopy: Counting the Carbons 13.7. Two-Dimensional (2D)-NMR 13.8. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 14: Organometallics 14.1. Organomagnesium Compounds 14.2. Grignard Reagents Are Bases and Nucleophiles 14.3. Organolithium Reagents 14.4. Organocuprates 14.5. Other Organometallic Compounds 14.6. Organization of Reaction Types 14.7. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 15: Oxidation 15.1. Defining an Oxidation 15.2. Oxidation of Alcohols 15.2.A. Chromium (VI) Oxidation of Alcohols 15.2.B. Swern Oxidation 15.3. Dihydroxylation of Alkenes 15.4. Epoxidation of Alkenes 15.5. Oxidative Cleavage 15.5. C—H Oxidation 15.6. Organization of Reaction Types 15.7. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 16: Reactions of Aldehydes and Ketones 16.1. Aldehydes and Ketones 16.2. The Reaction of Ketones and Aldehydes With Strong Nucleophiles 16.3. Stereoselectivity 16.4. The Reaction of Ketones and Aldehydes With Weak Nucleophiles 16.4.A. Reaction With Water 16.4.B. Reaction With Alcohols 16.4.C. Reaction With Amines 16.5. Organization of Reaction Types 16.6. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 17: Reduction 17.1 Defining a Reduction 17.2. Hydride Reducing Agents 17.3. Hydride Reduction of Other Functional Groups 17.4. Catalytic Hydrogenation 17.4.A. Hydrogenation of Alkenes and Alkynes 17.4.B. Homogeneous Hydrogenation 17.4.C. Hydrogenation of Heteroatom Functional Groups 17.5. Dissolving Metal Reductions 17.6. Organization of Reaction Types 17.7. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 18: Carboxylic Acid Derivatives and Acyl Substitution 18.1. Carboxylic Acids 18.2. Carboxylic Acid Derivatives: Structure and Nomenclature 18.3. Sulfonic Acids and Derivatives 18.4. Acyl Substitution and Hydrolysis of Carboxylic Acid Derivatives 18.5. Preparation of Acid Chlorides and Acid Anhydrides 18.6. Preparation of Esters 18.7. Baeyer-Villiger Oxidation 18.8. Preparation of Amides 18.9. Carboxylic Acid Derivatives React With Carbon Nucleophiles 18.10. Dicarboxylic Acid Derivatives 18.11. Nitrate Esters, Sulfate Esters, and Phosphate Esters 18.12. Nitriles Are Carboxylic Acid Derivatives 18.13. Fatty Acids and Lipids 18.14. Organization of Reaction Types 18.15. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 19: Aromatic Compounds and Benzene Derivatives 19.1. Benzene and Aromaticity 19.2. Functionalized Benzene Derivatives 19.2.A. Alkyl Substituents (Arenes) 19.2.B. Functional Groups on the Benzene Ring 19.3. Electrophilic Aromatic Substitution 19.3.A. Aromatic Substitution: Halogenation, Nitration, and Sulfonation 19.3.B. Friedel-Crafts Alkylation 19.3.C. Friedel-Crafts Acylation 19.4. Disubstituted Benzene Derivatives 19.4.A. Regioselectivity 19.4.B. Activating and Deactivating Substituents 19.4.C. Halogen Substituents 19.4.D. Aniline and Aniline Derivatives 19.5. Polysubstituted Benzene Derivatives 19.6. Aromatic Coupling Reactions 19.7. Reduction And Aromatic Compounds 19.8. Aromaticity in Monocyclic Molecules Other Than Benzene 19.9. Polynuclear Aromatic Hydrocarbons 19.9.A. Naphthalene, Anthracene, and Phenanthrene 19.9.B. Aromatic Substitution Reactions of Polycyclic Hydrocarbons 19.10. Nucleophilic Aromatic Substitution 19.11. Aromatic Amines and Diazonium Salts 19.12. Benzyne Intermediates 19.13. Synthesis of Aromatic Compounds 19.14. Spectroscopy of Aromatic Compounds 19.15. Organization of Reaction Types 19.16. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 20: Enolate Anions: Acyl Addition and Acyl Substitution 20.1. Aldehydes and Ketones Are Weak Acids 20.2. Non-nucleophilic Bases 20.3. Enolate Alkylation 20.4. The Aldol Condensation 20.5. The Zimmerman Model 20.6. The Intramolecular Aldol Condensation 20.7. Acid-Catalyzed Aldol Condensations 20.8. Ester Enolate Anions 20.8.A. Alkylation of Ester Enolate Anions 20.8.B. Acyl Substitution and Acyl Addition 20.8.C. Intramolecular Condensation: The Dieckmann Condensation 20.8.D. Malonic Ester Enolate Anions 20.9. Decarboxylation 20.10. The Knoevenagel Reaction, the Malonic Ester Synthesis, and the Acetoacetic Acid Synthesis 20.11. Yid Reactions 20.12. Organization of Reaction Types 20.13. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 21: Difunctional Molecules: Dienes and Conjugated Carbonyl Compounds 21.1. Conjugation 21.2. Photochemistry of C=C and C=O 21.3. Detecting Conjugation With Ultraviolet Spectroscopy 21.4. Reactions of Conjugated -Bonds 21.5. Conjugate Addition 21.6. Reduction of Conjugated Systems 21.7. Organization of Reaction Types 21.8. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 22. Difunctional Molecules: Pericyclic Reactions 22.1. The Diels-Alder Reaction 22.2. Reactivity of Dienes and Alkenes 22.3. Selectivity in the Diels-Alder Reaction 22.4. Other Pericyclic Reactions: [3+2] [2+2] 22.5. Sigmatropic Rearrangements 22.6. Organization of Reaction Types 22.7. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 23: Heteroaromatic Compounds 23.1. Nitrogen, Oxygen and Sulfur in an Aromatic Ring 23.2. Substitution Reactions in Monocyclic Heterocyclic Aromatic Compounds 23.3. Heteroaromatic Compounds With More Than One Ring 23.4. Aromatic Substitution Reactions of Polycyclic Heterocycles 23.5. Reduced Heterocycles 23.6. Alkaloids 23.7. Biological Relevance Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 24: Multifunctional Compounds: Amines, Amino Acids and Peptides 24.1. Reactions That Form Amines 24.2. Amino Acids 24.3. Reactions and Synthesis of -Amino Acids 24.4. Biological Relevance: Peptides 24.5. Biological Relevance: Proteins 24.6. Biological Relevance: Enzymes 24.7. Combinatorial Methods 24.8. Amino Acid Residue Identification in Proteins 24.9. End Group Analysis 24.10. Hormones Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK Chapter 25: Multifunctional Compounds: Carbohydrates 25.1. Polyhydroxy Carbonyl Compounds 25.1.A. Monosaccharides 25.1.B. Hemi-Acetals 25.1.C. The Anomeric Effect 25.1.D. Ketose Monosaccharides 25.1.E. Amino Sugars 25.2. Disaccharides, Trisaccharides, Oligosaccharides, and Polysaccharides 25.3. Reactions of Carbohydrates 25.4. Glycosides 25.5. Biological Relevance: Nucleosides and Nucleotides 25.6. Biological Relevance: Polynucleotides Correlation of Homework with Concepts ANSWERS TO IN-CHAPTER QUESTIONS HOMEWORK

Reviews from the Textbook & Authors Academic Association, 2025:"Organic Chemistry: An Acid-Base Approach, Third Edition" makes the complex subject of organic chemistry more approachable by using a foundation that chemistry students are familiar with from introductory chemistry (acid-base reactions) and expounding on it. It is clearly written and well-organized with many questions, prompts, and emphasized text to help readers focus on important concepts. It deserves to win the Textbook Excellence Award.Organic chemistry is an inherently dense and difficult subject for undergraduates, but this text explains it in clear, well-composed narrative. It stands out from other textbooks especially in easy navigability through active hyperlinks from the table of contents to the index and throughout the chapters. Smith's Organic Chemistry Third Edition also takes a very welcome historical approach to the subject, with a rich array of scientist profiles and attention to gender and ethnic diversity among important contributors to the science.Organic Chemistry: An Acid–Base Approach (Third Edition) by Michael B. Smith offers a unique acid–base approach that greatly improves a student’s understanding of nucleophiles and nucleophilic reactions. An exciting addition to this textbook revision includes research done by 35 current organic chemists whose cutting-edge work illustrates the breadth and variety of modern organic chemistry.