Enhanced descriptions from Syndetics:

Written for the short course-where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Fifth Edition provides an effective, clear, and readable introduction to the beauty and logic of organic chemistry. McMurry presents only those subjects needed for a brief course while maintaining the important pedagogical tools commonly found in larger books. With clear explanations, thought-provoking examples, and an innovative vertical format for explaining reaction mechanisms, FUNDAMENTALS takes a modern approach: primary organization is by functional group, beginning with the simple (alkanes) and progressing to the more complex. Within the primary organization, there is also an emphasis on explaining the fundamental mechanistic similarities of reactions. Through this approach, memorization is minimized and understanding is maximized. This new edition represents a major revision. The text has been revised at the sentence level to further improve clarity and readability; many new examples and topics of biological relevance have been added; and many new features have been introduced.

Table of contents provided by Syndetics

• Preface (p. xvi)
• A Note for Students (p. xxi)
• 1 Structure and Bonding; Acids and Bases (p. 1)
• 1.1 Atomic Structure (p. 3)
• 1.2 Electron Configuration of Atoms (p. 5)
• 1.3 Development of Chemical Bonding Theory (p. 6)
• 1.4 The Nature of Chemical Bonds (p. 7)
• 1.5 Forming Covalent Bonds: Valence Bond Theory (p. 10)
• 1.6 Hybridization: sp[superscript 3] Orbitals and the Structure of Methane (p. 11)
• 1.7 Hybridization: sp[superscript 3] Orbitals and the Structure of Ethane (p. 12)
• 1.8 Hybridization: sp[subscript 2] Orbitals and the Structure of Ethylene (p. 13)
• 1.9 Hybridization: sp Orbitals and the Structure of Acetylene (p. 16)
• 1.10 Polar Covalent Bonds: Electronegativity (p. 17)
• 1.11 Acids and Bases: The Bronsted--Lowry Definition (p. 20)
• 1.12 Acids and Bases: The Lewis Definition (p. 24)
• 2 The Nature of Organic Compounds: Alkanes (p. 34)
• 2.1 Functional Groups (p. 35)
• 2.2 Alkanes and Alkyl Groups: Isomers (p. 41)
• 2.3 Naming Branched-Chain Alkanes (p. 46)
• 2.4 Properties of Alkanes (p. 49)
• 2.5 Conformations of Ethane (p. 50)
• 2.6 Drawing Chemical Structures (p. 53)
• 2.7 Cycloalkanes (p. 54)
• 2.8 Cis--Trans Isomerism in Cycloalkanes (p. 55)
• 2.9 Conformations of Some Cycloalkanes (p. 57)
• 2.10 Axial and Equatorial Bonds in Cyclohexane (p. 60)
• 2.11 Conformational Mobility of Cyclohexane (p. 61)
• 3 The Nature of Organic Reactions: Alkenes (p. 74)
• 3.1 Naming Alkenes (p. 75)
• 3.2 Electronic Structure of Alkenes (p. 78)
• 3.3 Cis--Trans Isomers of Alkenes (p. 79)
• 3.4 Sequence Rules: The E,Z Designation (p. 81)
• 3.5 Kinds of Organic Reactions (p. 84)
• 3.6 How Reactions Occur: Mechanisms (p. 86)
• 3.7 The Mechanism of an Organic Reaction: Addition of HCl to Ethylene (p. 89)
• 3.8 Describing a Reaction: Reaction Energy Diagrams and Transition States (p. 92)
• 3.9 Describing a Reaction: Intermediates (p. 94)
• 4 Reactions of Alkenes and Alkynes (p. 105)
• 4.1 Addition of HX to Alkenes: Hydrohalogenation (p. 106)
• 4.2 Orientation of Alkene Addition Reactions: Markovnikov's Rule (p. 106)
• 4.3 Carbocation Structure and Stability (p. 109)
• 4.4 Addition of H[subscript 2]O to Alkenes: Hydration (p. 111)
• 4.5 Addition of X[subscript 2] to Alkenes: Halogenation (p. 113)
• 4.6 Addition of H[subscript 2] to Alkenes: Hydrogenation (p. 115)
• 4.7 Oxidation of Alkenes: Hydroxylation and Cleavage (p. 116)
• 4.8 Biological Addition Reactions of Alkenes (p. 118)
• 4.9 Addition of Radicals to Alkenes: Polymers (p. 119)
• 4.10 Conjugated Dienes (p. 122)
• 4.11 Stability of Allylic Carbocations: Resonance (p. 124)
• 4.12 Drawing and Interpreting Resonance Forms (p. 126)
• 4.13 Alkynes and Their Reactions (p. 128)
• 5 Aromatic Compounds (p. 143)
• 5.1 Structure of Benzene: The Kekule Proposal (p. 144)
• 5.2 Structure of Benzene: The Resonance Proposal (p. 145)
• 5.3 Naming Aromatic Compounds (p. 146)
• 5.4 Electrophilic Aromatic Substitution Reactions: Bromination (p. 149)
• 5.5 Other Electrophilic Aromatic Substitution Reactions (p. 153)
• 5.6 The Friedel--Crafts Alkylation and Acylation Reactions (p. 154)
• 5.7 Substituent Effects in Electrophilic Aromatic Substitution (p. 156)
• 5.8 An Explanation of Substituent Effects (p. 158)
• 5.9 Oxidation and Reduction of Aromatic Compounds (p. 162)
• 5.10 Polycyclic Aromatic Hydrocarbons (p. 163)
• 5.11 Organic Synthesis (p. 164)
• 6 Stereochemistry (p. 177)
• 6.1 Stereochemistry and the Tetrahedral Carbon (p. 178)
• 6.2 The Reason for Handedness in Molecules: Chirality (p. 180)
• 6.3 Optical Activity (p. 183)
• 6.4 Specific Rotation (p. 184)
• 6.5 Pasteur's Discovery of Enantiomers (p. 186)
• 6.6 Sequence Rules for Specifying Configuration (p. 187)
• 6.7 Diastereomers (p. 191)
• 6.8 Meso Compounds (p. 193)
• 6.9 Molecules with More Than Two Stereocenters (p. 195)
• 6.10 Racemic Mixtures and the Resolution of Enantiomers (p. 196)
• 6.11 Physical Properties of Stereoisomers (p. 199)
• 6.12 A Brief Review of Isomerism (p. 199)
• 6.13 Chirality in Nature (p. 201)
• 7 Alkyl Halides (p. 211)
• 7.1 Naming Alkyl Halides (p. 212)
• 7.2 Preparing Alkyl Halides (p. 213)
• 7.3 Reactions of Alkyl Halides: Grignard Reagents (p. 215)
• 7.4 Nucleophilic Substitution Reactions (p. 217)
• 7.5 The S[subscript N]2 Reaction (p. 220)
• 7.6 The S[subscript N]1 Reaction (p. 224)
• 7.7 Eliminations: The E2 Reaction (p. 228)
• 7.8 Eliminations: The E1 Reaction (p. 230)
• 7.9 A Summary of Reactivity: S[subscript N]1, S[subscript N]2, E1, E2 (p. 232)
• 7.10 Substitution Reactions in Living Organisms (p. 233)
• 8 Alcohols, Phenols, and Ethers (p. 243)
• 8.1 Naming Alcohols, Phenols, and Ethers (p. 244)
• 8.2 Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding (p. 246)
• 8.3 Properties of Alcohols and Phenols: Acidity (p. 248)
• 8.4 Synthesis of Alcohols (p. 250)
• 8.5 Reactions of Alcohols (p. 253)
• 8.6 Synthesis and Reactions of Phenols (p. 258)
• 8.7 Synthesis and Reactions of Ethers (p. 261)
• 8.8 Cyclic Ethers: Epoxides (p. 262)
• 8.9 Thiols and Sulfides (p. 264)
• 9 Aldehydes and Ketones: Nucleophilic Addition Reactions (p. 276)
• 9.1 The Nature of Carbonyl Compounds (p. 277)
• 9.2 Naming Aldehydes and Ketones (p. 279)
• 9.3 Synthesis of Aldehydes and Ketones (p. 281)
• 9.4 Oxidation of Aldehydes (p. 282)
• 9.5 Nucleophilic Addition Reactions of Aldehydes and Ketones: Reduction (p. 283)
• 9.6 Nucleophilic Addition of Water: Hydration (p. 285)
• 9.7 Nucleophilic Addition of Alcohols: Acetal Formation (p. 288)
• 9.8 Nucleophilic Addition of Amines: Imine Formation (p. 290)
• 9.9 Nucleophilic Addition of Grignard Reagents: Alcohol Formation (p. 291)
• 9.10 Conjugate Nucleophilic Addition Reactions (p. 294)
• 9.11 Some Biological Nucleophilic Addition Reactions (p. 295)
• 10 Carboxylic Acids and Derivatives (p. 305)
• 10.1 Naming Carboxylic Acids and Derivatives (p. 306)
• 10.2 Occurrence and Properties of Carboxylic Acids (p. 310)
• 10.3 Synthesis of Carboxylic Acids (p. 313)
• 10.4 Nucleophilic Acyl Substitution Reactions (p. 314)
• 10.5 Reactions of Carboxylic Acids (p. 317)
• 10.6 Chemistry of Acid Halides (p. 320)
• 10.7 Chemistry of Acid Anhydrides (p. 322)
• 10.8 Chemistry of Esters (p. 324)
• 10.9 Chemistry of Amides (p. 329)
• 10.10 Chemistry of Nitriles (p. 331)
• 10.11 Polymers from Carbonyl Compounds: Nylons and Polyesters (p. 334)
• 11 Carbonyl Alpha-Substitution Reactions and Condensation Reactions (p. 347)
• 11.1 Keto--Enol Tautomerism (p. 348)
• 11.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions (p. 352)
• 11.3 Alpha Halogenation of Aldehydes and Ketones (p. 353)
• 11.4 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation (p. 355)
• 11.5 Reactivity of Enolate Ions (p. 358)
• 11.6 Alkylation of Enolate Ions (p. 359)
• 11.7 Carbonyl Condensation Reactions (p. 362)
• 11.8 Condensations of Aldehydes and Ketones: The Aldol Reaction (p. 362)
• 11.9 Dehydration of Aldol Products: Synthesis of Enones (p. 364)
• 11.10 Condensations of Esters: The Claisen Condensation Reaction (p. 366)
• 11.11 Biological Carbonyl Reactions (p. 368)
• 12 Amines (p. 379)
• 12.1 Naming Amines (p. 380)
• 12.2 Structure and Properties of Amines (p. 383)
• 12.3 Basicity of Amines (p. 383)
• 12.4 Synthesis of Amines (p. 386)
• 12.5 Reactions of Amines (p. 392)
• 12.6 Heterocyclic Amines (p. 393)
• 12.7 Alkaloids: Naturally Occurring Amines (p. 397)
• 13 Structure Determination (p. 406)
• 13.1 Infrared Spectroscopy and the Electromagnetic Spectrum (p. 407)
• 13.2 Infrared Spectroscopy of Organic Molecules (p. 410)
• 13.3 Ultraviolet Spectroscopy (p. 415)
• 13.4 Interpreting Ultraviolet Spectra: The Effect of Conjugation (p. 416)
• 13.5 Nuclear Magnetic Resonance Spectroscopy (p. 418)
• 13.6 The Nature of NMR Absorptions (p. 419)
• 13.7 Chemical Shifts (p. 422)
• 13.8 Chemical Shifts in [superscript 1]H NMR Spectra (p. 423)
• 13.9 Integration of [superscript 1]H NMR Spectra: Proton Counting (p. 425)
• 13.10 Spin--Spin Splitting in [superscript 1]H NMR Spectra (p. 426)
• 13.11 Uses of [superscript 1]H NMR Spectra (p. 430)
• 13.12 [superscript 13]C NMR Spectroscopy (p. 430)
• 14 Biomolecules: Carbohydrates (p. 441)
• 14.1 Classification of Carbohydrates (p. 442)
• 14.2 Configurations of Monosaccharides: Fischer Projections (p. 444)
• 14.3 D,L Sugars (p. 446)
• 14.4 Configurations of Aldoses (p. 448)
• 14.5 Cyclic Structures of Monosaccharides: Hemiacetal Formation (p. 450)
• 14.6 Monosaccharide Anomers: Mutarotation (p. 452)
• 14.7 Reactions of Monosaccharides (p. 454)
• 14.9 Polysaccharides (p. 460)
• 14.10 Other Important Carbohydrates (p. 463)
• 14.11 Cell-Surface Carbohydrates and Carbohydrate Vaccines (p. 463)
• 15 Biomolecules: Amino Acids, Peptides, and Proteins (p. 472)
• 15.1 Structures of Amino Acids (p. 473)
• 15.2 Isoelectric Points (p. 478)
• 15.3 Peptides and Proteins (p. 481)
• 15.4 Covalent Bonding in Peptides (p. 482)
• 15.5 Peptide Structure Determination: Amino Acid Analysis (p. 484)
• 15.6 Peptide Sequencing: The Edman Degradation (p. 484)
• 15.7 Peptide Synthesis (p. 487)
• 15.8 Classification of Proteins (p. 490)
• 15.9 Protein Structure (p. 491)
• 15.10 Enzymes (p. 494)
• 15.11 How Do Enzymes Work? Citrate Synthase (p. 497)
• 16 Biomolecules: Lipids and Nucleic Acids (p. 507)
• 16.1 Lipids (p. 508)
• 16.2 Fats and Oils (p. 508)
• 16.3 Soaps (p. 511)
• 16.4 Phospholipids (p. 513)
• 16.5 Steroids (p. 515)
• 16.6 Nucleic Acids and Nucleotides (p. 517)
• 16.7 Structure of DNA (p. 520)
• 16.8 Base Pairing in DNA: The Watson--Crick Model (p. 521)
• 16.9 Nucleic Acids and Heredity (p. 524)
• 16.10 Replication of DNA (p. 524)
• 16.11 Structure and Synthesis of RNA: Transcription (p. 526)
• 16.12 RNA and Protein Biosynthesis: Translation (p. 527)
• 16.13 Sequencing DNA (p. 530)
• 16.14 The Polymerase Chain Reaction (p. 532)
• 17 The Organic Chemistry of Metabolic Pathways (p. 540)
• 17.1 An Overview of Metabolism and Biochemical Energy (p. 541)
• 17.2 Catabolism of Fats: [beta]-Oxidation Pathway (p. 544)
• 17.3 Catabolism of Carbohydrates: Glycolysis (p. 549)
• 17.4 The Citric Acid Cycle (p. 554)
• 17.5 Catabolism of Proteins: Transamination (p. 557)
• 17.6 The Organic Chemistry of Metabolic Pathways: A Summary (p. 559)
• Appendixes
• A Nomenclature of Polyfunctional Organic Compounds (p. 1)
• B Glossary (p. 8)
• C Answers to Selected In-Chapter Problems (p. 18)
• Index (p. 1)