Organic chemistry / David Klein.

Includes index.

Machine generated contents note: Chapter 1 - Electron Density. -- Part 1:Electrons, Orbitals, and Bonds. -- 1.1 Quantum Mechanics. -- 1.2 Atomic Orbitals. -- 1.2.a What are Atomic Orbitals? -- 1.2.b Phases of Atomic Orbitals. -- 1.2.c Filling Atomic Orbitals with Electrons. -- 1.3 Covalent Bonds: The Sharing of Electrons. -- 1.4 Valence Bond Theory and Hybridized Atomic Orbitals. -- 1.5 MO Theory. -- 1.6 Sigma Bonds. -- 1.7 Pi Bonds. -- 1.7a Double Bonds. -- 1.7b Triple Bonds. -- Part 2: Drawing and Interpreting Molecular Representations. -- 1.8 Molecular Representations. -- 1.9 Bond-Line Drawings. -- 1.9a How to Read Bond-Line Drawings. -- 1.9b How to draw Bond-Line Drawings. -- 1.9c Mistakes to avoid: -- 1.10 Identifying Formal Charges. -- 1.11 Identifying Lone Pairs that are not Drawn. -- Part 3: Drawing Resonance Structures. -- 1.12 What is Resonance? -- 1.13 Curved Arrows: The Tools for Drawing Resonance Structures. -- 1.14 Drawing Formal Charges in Resonance Structures. -- 1.15 Drawing Resonance Structures - By Recognizing Patterns. -- 1.16 Assessing Relative Importance of Resonance Structures. -- Chapter 2 - Nucleophiles, Electrophiles, Acids and Bases. -- Part 1: Nucleophiles and Electrophiles. -- 2.1 Induction and Polar Covalent Bonds. -- 2.2 Identifying Electrophilic Centers. -- 2.2.a Unfilled Octets. -- 2.2.b Induction. -- 2.2.c Resonance. -- 2.3 Identifying Nucleophilic Centers. -- 2.3.a Lone Pairs and Pi bonds. -- 2.3.b Induction. -- 2.3.c Resonance. -- Part 2: Acids and Bases. -- 2.4 Curved Arrow Notation: The flow of electron density. -- 2.5 Brønsted-Lowry Acidity: A Quantitative Perspective. -- 2.5.a Using pKa values to Compare Acidity. -- 2.5.b Using pKa values to Compare Basicity. -- 2.5.c Using pKa values to Predict the Position of Equilibrium. -- 2.6 Brønsted-Lowry Acidity: A Qualitative Perspective. -- 2.6.a Factor #1 - What atom is the charge on? -- 2.6.b Factor #2 - Resonance. -- 2.6.c Factor #3 - Induction. -- 2.6.d Factor #4 - Orbitals. -- 2.6.e Ranking the Four Factors. -- 2.7 Position of Equilibrium and Choosing Suitable Reagents. -- 2.8 Choice of Solvent. -- 2.9 Counter-Stabilizing Cations. -- 2.10 Lewis Acids and Bases. -- 2.1 Nucleophilicity vs. Basicity. -- Chapter 3 - Nomenclature and Molecular Constitution. -- Part 1: Nomenclature. -- 3.1 Identifying the Functional Group. -- 3.2 Identifying Unsaturation. -- 3.3 Selecting the Parent. -- 3.4 Naming Substituents. -- 3.5 Stereoisomerism. -- 3.6 Numbering the Parent Chain. -- 3.7 Assembling a complete name. -- 3.8 Extra Practice with Alkanes. -- 3.9 Naming Bicyclic Compounds. -- 3.10 Common Names accepted by IUPAC. -- 3.11 Pharmaceuticals. -- 3.12 Degree of Substitution. -- Part 2: Molecular Constitution. -- 3.13 Constitutional Isomerism. -- 3.14 Hydrogen Deficiency Index (HDI) - Degree of Unsaturation. -- 3.15 Relative Stability of Isomeric Alkanes. -- 3.16 Sources and Uses of Alkanes. -- Chapter 4 - Molecular Structure and Properties. -- Part 1: Molecular Geometry and Molecular Properties. -- 4.1 Predicting Geometry: VSEPR Theory. -- 4.1a Geometries resulting from sp3 hybridization. -- 4.1b Geometries resulting from sp2 hybridization. -- 4.1c Geometry resulting from sp hybridization. -- 4.2 Effect of Resonance on Geometry. -- 4.3 Three-Dimensional Representations. -- 4.4 Molecular Polarity. -- 4.5 Intermolecular Forces and Physical Properties. -- 4.5a Dipole-Dipole Interactions. -- 4.5b Hydrogen-Bonding. -- 4.5c Fleeting Dipole-Dipole Interactions. -- 4.6 Solubility. -- Part 2: Conformational Analysis of Alkanes and Cycloalkanes. -- 4.7 Newman Projections. -- 4.8 Conformational Analysis of Ethane and Propane. -- 4.9 Conformational Analysis of Butane. -- 4.10 Cycloalkanes. -- 4.10a Cyclopropane. -- 4.10b Cylcobutane. -- 4.10c Cyclopentane. -- 4.11 Conformations of Cyclohexane. -- 4.12 Drawing Chair Conformations. -- 4.12a Drawing the skeleton of a Chair Conformation. -- 4.12b Drawing Axial and Equatorial Substituents. -- 4.13 Monosubstituted Cyclohxanes. -- 4.13a Drawing both Chair Conformations. -- 4.13b Comparing the Stability of both Chair Conformations. -- 4.14 Disubstituted Cyclohexanes. -- 4.14a Drawing both Chair Conformations. -- 4.14b Comparing Stability of both Chair Conformations. -- 4.15 Cis-trans Stereoisomerism. -- 4.16 Polycyclic Systems. -- Chapter 5 - Stereoisomerism. -- 5.1 Designating Configuration Using the Cahn-Ingold-Prelog System. -- 5.2 Designating Configuration Using the Cahn-Ingold-Prelog System. -- 5.2a Assigning priorities to all four groups. -- 5.2b Rotating the molecule so that the fourth priority is on a dash. -- 5.2c The E-Z system. -- 5.3 Biological Significance of Chirality. -- 5.4 Optical Activity. -- 5.4a Plane polarized light. -- 5.4b Polarimetry. -- 5.4c Source of optical activity. -- 5.4d Specific Rotation. -- 5.4e Enantiomeric Excess. -- 5.5 Stereoisomeric Relationships: Enantiomers and Diasteromers. -- 5.6 Symmetry and Chirality. -- 5.6a Rotational Symmetry. -- 5.6b Reflectional Symmetry. -- 5.6c Chirality is Dependent on the Absence of Reflectional Symmetry. -- 5.6d Meso Compounds. -- 5.7 Conformationally mobile systems. -- 5.8 Fischer Projections. -- 5.9 Resolution of Enantiomers. -- 5.9a Resolution via Crystallization. -- 5.9b Chiral Resolving agents. -- 5.9c Chiral Column Chromatography. -- 5.10 Application: Chiral Drugs. -- Chapter 6 - Chemical Reactivity and Mechanisms. -- 6.1 Enthalpy. -- 6.2 Entropy. -- 6.3 Gibbs Free Energy. -- 6.4 Equilibria. -- 6.5 Kinetics. -- 6.5a Rate Equations. -- 6.5b Factors Affecting the Rate constant. -- 6.5c Catalysts and Enzymes. -- 6.6 Reading Energy Diagrams. -- 6.6a Thermodynamics vs. kinetics. -- 6.6b Transition States vs. Intermediates. -- 6.6c The Hammond Postulate. -- 6.7 Mechanisms and Curved Arrows: Electron Transfer Steps. -- 6.7a Nucleophilic Attack. -- 6.7b Loss of a Leaving group. -- 6.7c Proton Transfers. -- 6.7d Rearrangements. -- 6.8 Combining the Fundamental Electron Transfer Steps. -- 6.9 Drawing Curved Arrows. -- 6.10 Carbocation Rearrangements. -- Chapter 7 - Substitution and Elimination Reactions. -- Part 1: Substitution reactions. -- Properties of Alkyl Halides. -- SN1 Mechanism vs. SN2 Mechanism. -- Determining the Effect of the Electrophile (Substrate). -- Determining the Effect of the Nucleophile. -- Determining the Effect of the Leaving Group. -- Determining the Effect of the Solvent. -- Predicting which Mechanism will Predominate. -- Predicting Products and Proposing Mechanisms. -- Part 2: Elimination Reactions. -- E1 vs. E2 Mechanisms. -- Identifying the Key Differences between the E1 and E2 Mechanisms. -- Predicting the Regiochemistry of an E1 or E2 Reaction. -- Predicting the Stereochemistry of an E1 or E2 Reaction. -- Determining the Effect of the Electrophile (Substrate). -- Determining the Effect of the Base. -- Predicting which Mecha

"Each chapter contains strategically positioned sections that cover important skills. In each section, an important skill is developed or fine-tuned. Multiple problems are then provided in order to build competence in that skill. Students are given the opportunity to master each core skill before moving on to the next section. The end-of-chapter exercises integrate the skills developed throughout the chapter. Three short chapters (Chapters 7, 12, and 24) are devoted entirely to skill development (proposing mechanisms and proposing syntheses). WileyPLUS incorporates hundreds of end of chapter problems all of which are available with multiple forms of problem solving support (link to text, tutorials, videos, etc.). Dr. Klein's writing style strikes a unique balance between a formal and conversational tone, while not comprising the scientific rigor expected of a 2-semester organic chemistry text."--