Organic Chemistry

Students often say, “I studied 40 hours for this exam and I still didn’t do well. Where did I go wrong?” Most instructors hear this complaint every year. In many cases, it is true that the student invested countless hours, only to produce abysmal results. Often, inefficient study habits are to blame. The important question is: why do so many students have difficulty preparing themselves for organic chemistry exams? There are certainly several factors at play here, but perhaps the most dominant factor is a fundamental disconnect between what students learn and the tasks expected of them. To address the disconnect in organic chemistry instruction, David Klein has developed a textbook that utilizes a skills-based approach to instruction. The textbook includes all of the concepts typically covered in an organic chemistry textbook, but special emphasis is placed on skills development to support these concepts. This emphasis upon skills development will provide students with a greater opportunity to develop proficiency in the key skills necessary to succeed in organic chemistry. As an example, resonance structures are used repeatedly throughout the course, and students must become masters of resonance structures early in the course. Therefore, a significant portion of chapter 1 is devoted to drawing resonance structures. Two chapters (6 and 12) are devoted almost entirely to skill development. Chapter 6 emphasizes skills that are necessary for drawing mechanisms, while chapter 12 prepares the student for proposing syntheses. In addition, each chapter contains numerous Skillbuilders, each of which is designed to foster a specific skill. Each skillbuildercontains three parts: 1. Learn the Skill: a solved problem that demonstrates a particular skill; 2. Practice the Skill: numerous problems (similar to the solved problem) that give the students an opportunity to practice and master the skill; 3. Apply the Skill: one or two more-challenging problems in which the student must apply the skill in a slightly different environment. These problems include conceptual, cumulative, and applied problems that encourage students to think out of the box. Sometimes problems that foreshadow concepts introduced in later chapters are also included. All SkillBuilders are visually summarized at the end of each chapter (Skillbuilder review), followed by a list of suggested in-chapter and end-of-chapter practice problems. David Klein is a lecturer at Johns Hopkins University where he teaches Organic and General Chemistry. He is a dynamic and creative teacher and uses analogy to help students grasp difficult topics. Klein’s unique informal voice and manner of presentation help students truly master key topics in this course. He is also the author of Organic Chemistry as a Second Language and General Chemistry as a Second Language , which have both been highly successful. 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 Students often say, “I studied 40 hours for this exam and I still didn’t do well. Where did I go wrong?” Mostinstructors hear this complaint every year. In many cases, it is true that the student invested countless hours, only to students have difficulty preparing themselves for organic chemistry exams? There are certainly several factors at __disconnect__ tasks expected of them. To address the disconnect in organic chemistry instruction, David Klein has developed a textbook that utilizes a skills-based approach to instruction. The textbook includes all of the concepts typically covered in an organic chemistry textbook, but special emphasis is placed on skills development to support these concepts. This emphasis upon skills development will provide students with a greater opportunity to develop proficiency in the key skills necessary to succeed in organic chemistry. As an example, resonance structures are used repeatedly throughout the course, and students must become masters of resonance structures early in the course. Therefore, a significant portion of chapter 1 is devoted to drawing resonance structures. Two chapters (6 and 12) are devoted almost entirely to skill development. Chapter 6 emphasizes skills that are necessary for drawing mechanisms, while chapter 12 prepares the student for proposing syntheses. In addition, each chapter contains numerous Skillbuilders, each of which is designed to foster a specific skill. Each skillbuildercontains three parts:1. Learn the Skill: a solved problem that demonstrates a particular skill; 2. Practice the Skill: numerous problems (similar to the solved problem) that give the students an opportunity to practice and master the skill; 3. Apply the Skill: one or two more-challenging problems in which the student must apply the skill in a slightly different environment. These problems include conceptual, cumulative, and applied problems that encourage students to think out of the box. Sometimes problems that foreshadow concepts introduced in later chapters are also included. All SkillBuilders are visually summarized at the end of each chapter (Skillbuilder review), followed by a list of suggested in-chapter and end-of-chapter practice problems. "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."-- Provided by publisher Success in organic chemistry requires mastery in two core aspects: fundamental concepts and the skills needed to apply those concepts and solve problems. With Organic Chemistry, Student Solution Manual and Study Guide, 4th Edition , students can learn to become proficient at approaching new situations methodically, based on a repertoire of skills. These skills are vital for successful problem solving in organic chemistry.