Organic chemistry / / Leroy G. Wade, Jr. ; contributing author, Jan William Simek

• Autore: Wade L. G. <1947->
• Pubblicazione: Harlow, England : , : Pearson, , [2017]; ©2017
• Edizione: Ninth, global edition.
• Descrizione fisica: 1 online resource (1,398 pages) : illustrations (some color), photographs, tables
• Disciplina: 547
• Soggetto topico: Chemistry, Organic
• Persona (resp. second.): SimekJan William
• Note generali: Includes index.
• Nota di contenuto: Cover -- Title Page 1 -- Copyright Page 2 -- About the Authors 3 -- Contents 5 -- Preface 25 -- 1 STRUCTURE AND BONDING 37 -- 1-1 The Origins of Organic Chemistry 37 -- 1-2 Principles of Atomic Structure 39 -- 1-3 Bond Formation: The Octet Rule 43 -- 1-4 Lewis Structures 44 -- 1-5 Multiple Bonding 45 -- Summary: Common Bonding Patterns (Uncharged) 45 -- 1-6 Electronegativity and Bond Polarity 46 -- 1-7 Formal Charges 47 -- 1-8 Ionic Structures 49 -- 1-9 Resonance 50 -- PROBLEM-SOLVING STRATEGY: Drawing and Evaluating Resonance Forms 54 -- 1-10 Structural Formulas 58 -- 1-11 Molecular Formulas and Empirical Formulas 61 -- 1-12 Wave Properties of Electrons in Orbitals 63 -- 1-13 Molecular Orbitals 64 -- 1-14 Pi Bonding 67 -- 1-15 Hybridization and Molecular Shapes 68 -- 1-16 Drawing Three-Dimensional Molecules 72 -- 1-17 General Rules of Hybridization and Geometry 73 -- Summary: Hybridization and Geometry 73 -- 1-18 Bond Rotation 78 -- 1-19 Isomerism 80 -- Essential Terms 83 -- Study Problems 86 -- 2 ACIDS AND BASES -- FUNCTIONAL GROUPS 91 -- 2-1 Polarity of Bonds and Molecules 92 -- 2-2 Intermolecular Forces 96 -- 2-3 Polarity Effects on Solubilities 100 -- 2-4 Arrhenius Acids and Bases 103 -- 2-5 Brønsted-Lowry Acids and Bases 104 -- 2-6 Strengths of Acids and Bases 105 -- 2-7 Equilibrium Positions of Acid-Base Reactions 109 -- PROBLEM-SOLVING STRATEGY: Predicting Acid-Base Equilibrium Positions 111 -- 2-8 Solvent Effects on Acidity and Basicity 112 -- Summary: Acidity and Basicity Limitations in Common Solvents 114 -- 2-9 Effects of Size and Electronegativity on Acidity 114 -- 2-10 Inductive Effects on Acidity 116 -- 2-11 Hybridization Effects on Acidity 117 -- 2-12 Resonance Effects on Acidity and Basicity 119 -- 2-13 Lewis Acids and Bases 122 -- 2-14 The Curved-Arrow Formalism 124 -- 2-15 Hydrocarbons 126. ; 2-16 Functional Groups with Oxygen 129 -- 2-17 Functional Groups with Nitrogen 132 -- Essential Terms 134 -- Study Problems 137 -- 3 STRUCTURE AND STEREOCHEMISTRY OF ALKANES 143 -- 3-1 Classification of Hydrocarbons (Review) 144 -- 3-2 Molecular Formulas of Alkanes 144 -- 3-3 Nomenclature of Alkanes 146 -- Summary: Rules for Naming Alkanes 151 -- 3-4 Physical Properties of Alkanes 153 -- 3-5 Uses and Sources of Alkanes 154 -- 3-6 Reactions of Alkanes 157 -- 3-7 Structure and Conformations of Alkanes 158 -- 3-8 Conformations of Butane 162 -- 3-9 Conformations of Higher Alkanes 165 -- 3-10 Cycloalkanes 165 -- 3-11 Cis-trans Isomerism in Cycloalkanes 167 -- 3-12 Stabilities of Cycloalkanes -- Ring Strain 168 -- 3-13 Cyclohexane Conformations 172 -- PROBLEM-SOLVING STRATEGY: Drawing Chair Conformations 174 -- 3-14 Conformations of Monosubstituted Cyclohexanes 176 -- 3-15 Conformations of Disubstituted Cyclohexanes 179 -- PROBLEM-SOLVING STRATEGY: Recognizing Cis and Trans Isomers 179 -- 3-16 Bicyclic Molecules 182 -- Essential Terms 184 -- Study Problems 188 -- 4 THE STUDY OF CHEMICAL REACTIONS 191 -- 4-1 Introduction 191 -- 4-2 Chlorination of Methane 192 -- 4-3 The Free-Radical Chain Reaction 193 -- 4-4 Equilibrium Constants and Free Energy 197 -- 4-5 Enthalpy and Entropy 199 -- 4-6 Bond-Dissociation Enthalpies 201 -- 4-7 Enthalpy Changes in Chlorination 202 -- 4-8 Kinetics and the Rate Equation 205 -- 4-9 Activation Energy and the Temperature Dependence of Rates 207 -- 4-10 Transition States 208 -- 4-11 Rates of Multistep Reactions 210 -- 4-12 Temperature Dependence of Halogenation 211 -- 4-13 Selectivity in Halogenation 212 -- 4-14 Hammond's Postulate 218 -- PROBLEM-SOLVING STRATEGY: Proposing Reaction Mechanisms 219 -- 4-15 Radical Inhibitors 222 -- 4-16 Reactive Intermediates 223 -- Summary: Reactive Intermediates 230 -- Essential Terms 230. ; Study Problems 233 -- 5 STEREOCHEMISTRY 237 -- 5-1 Introduction 237 -- 5-2 Chirality 238 -- 5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms 244 -- 5-4 Optical Activity 249 -- 5-5 Biological Discrimination of Enantiomers 254 -- 5-6 Racemic Mixtures 255 -- 5-7 Enantiomeric Excess and Optical Purity 256 -- 5-8 Chirality of Conformationally Mobile Systems 257 -- 5-9 Chiral Compounds Without Asymmetric Atoms 260 -- 5-10 Fischer Projections 262 -- Summary: Fischer Projections and Their Use 266 -- 5-11 Diastereomers 266 -- Summary: Types of Isomers 268 -- 5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons 269 -- 5-13 Meso Compounds 269 -- 5-14 Absolute and Relative Configuration 271 -- 5-15 Physical Properties of Diastereomers 273 -- 5-16 Resolution of Enantiomers 274 -- Essential Terms 277 -- Study Problems 280 -- 6 ALKYL HALIDES -- NUCLEOPHILIC SUBSTITUTION 283 -- 6-1 Introduction 283 -- 6-2 Nomenclature of Alkyl Halides 284 -- 6-3 Common Uses of Alkyl Halides 286 -- 6-4 Structure of Alkyl Halides 288 -- 6-5 Physical Properties of Alkyl Halides 289 -- 6-6 Preparation of Alkyl Halides 291 -- Summary: Methods for Preparing Alkyl Halides 295 -- 6-7 Reactions of Alkyl Halides: Substitution and Elimination 296 -- 6-8 Bimolecular Nucleophilic Substitution: The SN2 Reaction 297 -- 6-9 Generality of the SN2 Reaction 299 -- Summary: SN2 Reactions of Alkyl Halides 300 -- 6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile 301 -- Summary: Trends in Nucleophilicity 302 -- 6-11 Reactivity of the Substrate in SN2 Reactions 305 -- 6-12 Stereochemistry of the SN2 Reaction 309 -- 6-13 Unimolecular Nucleophilic Substitution: The SN1 Reaction 311 -- 6-14 Stereochemistry of the SN1 Reaction 315 -- 6-15 Rearrangements in SN1 Reactions 317 -- 6-16 Comparison of SN1 and SN2 Reactions 320 -- Summary: Nucleophilic Substitutions 322. ; Summary: Reactions of Alkyl Halides 323 -- Essential Terms 324 -- Study Problems 327 -- 7 STRUCTURE AND SYNTHESIS OF ALKENES -- ELIMINATION 332 -- 7-1 Introduction 332 -- 7-2 The Orbital Description of the Alkene Double Bond 333 -- 7-3 Elements of Unsaturation 335 -- 7-4 Nomenclature of Alkenes 337 -- 7-5 Nomenclature of Cis-Trans Isomers 339 -- Summary: Rules for Naming Alkenes 341 -- 7-6 Commercial Importance of Alkenes 342 -- 7-7 Physical Properties of Alkenes 344 -- 7-8 Stability of Alkenes 346 -- 7-9 Formation of Alkenes by Dehydrohalogenation of Alkyl Halides 354 -- 7-10 Unimolecular Elimination: The E1 Reaction 355 -- Summary: Carbocation Reactions 359 -- 7-11 Positional Orientation of Elimination: Zaitsev's Rule 360 -- 7-12 Bimolecular Elimination: The E2 Reaction 362 -- 7-13 Bulky Bases in E2 Eliminations -- Hofmann Orientation 364 -- 7-14 Stereochemistry of the E2 Reaction 365 -- 7-15 E2 Reactions in Cyclohexane Systems 368 -- 7-16 Comparison of E1 and E2 Elimination Mechanisms 370 -- Summary: Elimination Reactions 371 -- Summary: Substitution and Elimination Reactions of Alkyl Halides 374 -- PROBLEM-SOLVING STRATEGY: Predicting Substitutions and Eliminations 376 -- 7-18 Alkene Synthesis by Dehydration of Alcohols 377 -- 7-19 Alkene Synthesis by High-Temperature Industrial Methods 380 -- PROBLEM-SOLVING STRATEGY: Proposing Reaction Mechanisms 382 -- Summary: Methods for Synthesis of Alkenes 385 -- Essential Terms 386 -- Study Problems 389 -- 8 REACTIONS OF ALKENES 395 -- 8-1 Reactivity of the Carbon-Carbon Double Bond 395 -- 8-2 Electrophilic Addition to Alkenes 396 -- 8-3 Addition of Hydrogen Halides to Alkenes 398 -- 8-4 Addition of Water: Hydration of Alkenes 406 -- 8-5 Hydration by Oxymercuration-Demercuration 408 -- 8-6 Alkoxymercuration-Demercuration 411 -- 8-7 Hydroboration of Alkenes 412 -- 8-8 Addition of Halogens to Alkenes 418. ; 8-9 Formation of Halohydrins 421 -- 8-10 Catalytic Hydrogenation of Alkenes 425 -- 8-11 Addition of Carbenes to Alkenes 427 -- 8-12 Epoxidation of Alkenes 429 -- 8-13 Acid-Catalyzed Opening of Epoxides 431 -- 8-14 Syn Dihydroxylation of Alkenes 434 -- 8-15 Oxidative Cleavage of Alkenes 436 -- 8-16 Polymerization of Alkenes 439 -- 8-17 Olefin Metathesis 443 -- PROBLEM-SOLVING STRATEGY: Organic Synthesis 446 -- Summary: Reactions of Alkenes 448 -- Summary: Electrophilic Additions to Alkenes 451 -- Summary: Oxidation and Cyclopropanation Reactions of Alkenes 452 -- Essential Terms 453 -- Study Problems 457 -- 9 ALKYNES 464 -- 9-1 Introduction 464 -- 9-2 Nomenclature of Alkynes 465 -- 9-3 Physical Properties of Alkynes 467 -- 9-4 Commercial Importance of Alkynes 467 -- 9-5 Electronic Structure of Alkynes 469 -- 9-6 Acidity of Alkynes -- Formation of Acetylide Ions 470 -- 9-7 Synthesis of Alkynes from Acetylides 472 -- 9-8 Synthesis of Alkynes by Elimination Reactions 475 -- Summary: Syntheses of Alkynes 477 -- 9-9 Addition Reactions of Alkynes 477 -- 9-10 Oxidation of Alkynes 486 -- PROBLEM-SOLVING STRATEGY: Multistep Synthesis 488 -- Summary: Reactions of Alkynes 490 -- Summary: Reactions of Terminal Alkynes 491 -- Essential Terms 492 -- Study Problems 493 -- 10 STRUCTURE AND SYNTHESIS OF ALCOHOLS 496 -- 10-1 Introduction 496 -- 10-2 Structure and Classification of Alcohols 496 -- 10-3 Nomenclature of Alcohols and Phenols 497 -- 10-4 Physical Properties of Alcohols 502 -- 10-5 Commercially Important Alcohols 504 -- 10-6 Acidity of Alcohols and Phenols 506 -- 10-7 Synthesis of Alcohols: Introduction and Review 510 -- Summary: Previous Alcohol Syntheses 510 -- 10-8 Organometallic Reagents for Alcohol Synthesis 511 -- 10-9 Reactions of Organometallic Compounds 514 -- Summary: Grignard Reactions 520. ; 10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides 522.
• Sommario/riassunto: For courses in Organic Chemistry (2-Semester) A Student-Centered Approach to Learning and Studying Organic ChemistryWade & Simek's Ninth Edition of Organic Chemistry presents key principles of organic chemistry in the context of fundamental reasoning and problem solving. Authored to complement how students use a textbook today, new Problem Solving Strategies, Partially Solved Problems, Visual Reaction Guides and Reaction Starbursts encourage students to use the text before class as a primary introduction to organic chemistry as well as a comprehensive study tool for working problems and/or preparing for exams. With unparalleled and highly refined pedagogy, this Ninth edition gives students a contemporary overview of organic principles and the tools for organizing and understanding reaction mechanisms and synthetic organic chemistry. MasteringChemistry™ not included. Students, if MasteringChemistry is a recommended/mandatory component of the course, please ask your instructor for the correct ISBN and course ID. MasteringChemistry should only be purchased when required by an instructor. Instructors, contact your Pearson representative for more information. MasteringChemistry is an online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics™. .&nbsp.
• Titolo autorizzato: Organic chemistry
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Inglese
• Record Nr.: 9910154956203321
• Lo trovi qui: Univ. Federico II
• Serie: Always learning.