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Organic Chemistry is unusual among market-leading texts; it exists only as a brief text and is specifically designed for a one-semester short course in organic chemistry. Its heavy emphasis on applications, increased coverage of basic concepts, thorough problem-solving pedagogy, and comprehensive problem sets address the specific needs of students in this course."A Closer Look At" features require students to use resources on the Web to expand concepts in the text, applying text content more directly to real-world examples.The HM ClassPrep instructor CD-ROM provides valuable supplemental content in one convenient, portable product. The CD-ROM includes a test bank, Instructor s Resource Manual, and PowerPoint slides of all line art from the text and animations from the student CD-ROM.

Tabla de contenidos provista por Syndetics

• 1 Bonding and Isomerism
• 1.1 How Electrons Are Arranged in Atoms
• 1.2 Ionic and Covalent Bonding
• 1.3 Carbon and the Covalent Bond
• 1.4 Carbon-Carbon Single Bonds
• 1.5 Polar Covalent Bonds
• 1.6 Multiple Covalent Bonds
• 1.7 Valence
• 1.8 Isomerism
• 1.9 Writing Structural Formulas
• 1.10 Abbreviated Structural Formulas
• 1.11 Formal Charge
• 1.12 Resonance
• 1.13 Arrow Formalism
• 1.14 The Orbital View of Bonding; the Sigma Bond
• 1.15 Carbon sp3 Hybrid Orbitals
• 1.16 Tetrahedral Carbon; the Bonding in Methane
• 1.17 Classification According to Molecular Framework
• 1.18 Classification According to Functional Group Additional Problems
• 2 Alkanes and Cycloalkanes: Conformational and Geometric Isomerism
• 2.1 The Structures of Alkanes
• 2.2 Nomenclature of Organic Compounds
• 2.3 IUPAC Rules for Naming Alkanes
• 2.4 Alkyl and Halogen Substituents
• 2.5 Use of the IUPAC Rules
• 2.6 Sources of Alkanes A Closer Look At: Natural Gas
• 2.7 Physical Properties of Alkanes and Nonbonding Intermolecular Interactions A Closer Look At: Hydrogen Bonding
• 2.8 Conformations of Alkanes
• 2.9 Cycloalkane Nomenclature and Conformation
• 2.10 Cis-trans Isomerism in Cycloalkanes
• 2.11 Summary of Isomerism A Word About: Isomers, Possible and Impossible
• 2.12 Reactions of Alkanes A Word About: Methane, Marsh Gas, and Miller's Experiment
• 2.13 The Free-Radical Chain Mechanism of Halogenation Reaction Summary Mechanism Summary Additional Problems
• 3 Alkenes and Alkynes
• 3.1 Definition and Classification
• 3.2 Nomenclature
• 3.3 Some Facts About Double Bonds
• 3.4 The Orbital Model of a Double Bond; the Pi Bond
• 3.5 Cis-trans Isomerism in Alkenes A Word About: The Chemistry of Vision
• 3.6 Addition and Substitution Reactions Compared
• 3.7 Polar Addition Reactions
• 3.8 Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule
• 3.9 Mechanism of Electrophilic Addition to Alkenes
• 3.10 Markovnikov's Rule Explained
• 3.11 Reaction Equilibrium: What Makes a Reaction Go?
• 3.12 Reaction Rates: How Fast Does a Reaction Go?
• 3.13 Hydroboration of Alkenes
• 3.14 Addition of Hydrogen
• 3.15 Additions to Conjugated Systems
• 3.16 Free-Radical Additions; Polyethylene
• 3.17 Oxidation of Alkenes A Word About: Ethylene: Raw Material and Plant Hormone
• 3.18 Some Facts About Triple Bonds
• 3.19 The Orbital Model of a Triple Bond
• 3.20 Additon Reactions of Alkynes A Word About: Petroleum, Gasoline, and Octane Number A Closer Look At: Petroleum
• 3.21 Acidity of Alkynes Reaction Summary Mechanism Summary Additional Problems
• 4 Aromatic Compounds
• 4.1 Some Facts About Benzene
• 4.2 The Kekulea Structure of Benzene
• 4.3 The Resonance Model for Benzene
• 4.4 Orbital Model for Benzene
• 4.5 Symbols for Benzene
• 4.6 Nomenclature of Aromatic Compounds
• 4.7 The Resonance Energy of Benzene
• 4.8 Electrophilic Aromatic Substitution
• 4.9 The Mechanism of Electrophilic Aromatic Substitution
• 4.10 Ring-Activating and Ring-Deactivating Substituents
• 4.11 Ortho, Para-Directing, and Meta-Directing Groups
• 4.12 The Importance of Directing Effects in Synthesis
• 4.13 Polycyclic Aromatic Hydrocarbons A Word About: Polycyclic Aromatic Hydrocarbons and Cancer A Word About: C60, an Aromatic Sphere: The Fullerenes A Closer Look At: Polycyclic Aromatic Hydrocarbons Reaction Summary Mechanism Summary Additional Problems
• 5 Stereoisomerism
• 5.1 Chirality and Enantiomers
• 5.2 Stereogenic Centers; the Stereogenic Carbon Atom
• 5.3 Configuration and the R-S Convention
• 5.4 The E-Z Convention for Cis-trans Isomers
• 5.5 Polarized Light and Optical Activity A Word About: Pasteur's Experiments and the van't Hoff-LeBel Explanation
• 5.6 Properties of Enantiomers
• 5.7 Fischer Projection Formulas
• 5.8 Compounds with More Than One Stereogenic Center; Diastereomers
• 5.9 Meso Compounds; the Stereoisomers of Tartaric Acid
• 5.10 Stereochemistry; a Recap of Definitions
• 5.11 Stereochemistry and Chemical Reactions A Word About: Enantiomers and Biological Activity
• 5.12 Resolution of a Racemic Mixture A Closer Look At: Thalidomide Additional Problems
• 6 Organic Halogen Compounds; Substitution and Elimination Reactions
• 6.1 Nucleophilic Substitution
• 6.2 Examples of Nucleophilic Substitution
• 6.3 Nucleophilic Substitution Mechanism
• 6.4 The SN2 Mechanism
• 6.5 The SN1 Mechanism
• 6.6 The SN1 and SN2 Mechanisms Compared A Word About: SN2 Reactions in Nature: Biological Methylations
• 6.7 Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms
• 6.8 Substitution and Elimination in Competition
• 6.9 Polyhalogenated Aliphatic Compounds A Word About: CFCs, the Ozone Layer, and Trade-Offs A Word About: Halogenated Organic Compounds from the Sea Reaction Summary Mechanism Summary Additional Problems
• 7 Alcohols, Phenols, and Thiols
• 7.1 Nomenclature of Alcohols A Word About: Industrial Alcohols
• 7.2 Classification of Alcohols
• 7.3 Nomenclature of Phenols
• 7.4 Hydrogen Bonding in Alcohols and Phenols
• 7.5 Acidity and Basicity Reviewed
• 7.6 The Acidity of Alcohols and Phenols
• 7.7 The Basicity of Alcohols and Phenols
• 7.8 Dehydration of Alcohols to Alkenes
• 7.9 The Reaction of Alcohols with Hydrogen Halides
• 7.10 Other Ways to Prepare Alkyl Halides from Alcohols
• 7.11 A Comparison of Alcohols and Phenols
• 7.12 Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids A Word About: Biologically Important Alcohols and Phenols
• 7.13 Alcohols with More Than One Hydroxyl Group
• 7.14 Aromatic Substitution in Phenols A Word About: Quinones and the Bombardier Beetle
• 7.15 Oxidation of Phenols
• 7.16 Phenols as Antioxidants
• 7.17 Thiols, the Sulfur Analogs of Alcohols and Phenols A Word About: Hair, Curly or Straight Reaction Summary Additional Problems
• 8 Ethers and Epoxides
• 8.1 Nomenclature of Ethers
• 8.2 Physical Properties of Ethers
• 8.3 Ethers as Solvents
• 8.4 The Grignard Reagent; an Organometallic Compound
• 8.5 Preparation of Ethers A Closer Look At: MTBE
• 8.6 Cleavage of Ethers A Word About: Ether and Anesthesia
• 8.7 Epoxides (Oxiranes) A Word About: The Gypsy Moth's Epoxide
• 8.8 Reactions of Epoxides
• 8.9 Cyclic Ethers Reaction Summary Additional Problems
• 9 Aldehydes and Ketones
• 9.1 Nomenclature of Aldehydes and Ketones
• 9.2 Some Common Aldehydes and Ketones
• 9.3 Synthesis of Aldehydes and Ketones
• 9.4 Aldehydes and Ketones in Nature
• 9.5 The Carbonyl Group
• 9.6 Nucleophilic Addition to Carbonyl Groups; an Overview
• 9.7 Addition of Alcohols: Formation of Hemiacetals and Acetals
• 9.8 Addition of Water; Hydration of Aldehydes and Ketones
• 9.9 Addition of Grignard Reagents and Acetylides
• 9.10 Addition of Hydrogen Cyanide; Cyanohydrins
• 9.11 Addition of Nitrogen Nucleophiles
• 9.12 Reduction of Carbonyl Compounds
• 9.13 Oxidation of Carbonyl Compounds
• 9.14 Keto-Enol Tautomerism
• 9.15 Acidity of a-Hydrogens; the Enolate Anion
• 9.16 Deuterium Exchanges in Carbonyl Compounds
• 9.17 The Aldol Condensation
• 9.18 The Mixed Aldol Condensation A Word About: Water Treatment and the Chemistry of Enols/Enolates
• 9.19 Commercial Syntheses via the Aldol Condensation Reaction Summary Mechanism Summary Additional Problems
• 10 Carboxylic Acids and Their Derivatives
• 10.1 Nomenclature of Acids
• 10.2 Physical Properties of Acids
• 10.3 Acidity and Acidity Constants
• 10.4 What Makes Carboxylic Acids Acidic?
• 10.5 Effect of Structure on Acidity; the Inductive Effect Revisited
• 10.6 Conversion of Acids to Salts
• 10.7 Preparation o