Organic chemistry

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 complem...

Descripción completa

Detalles Bibliográficos
Otros Autores:	Wade, L. G., 1947- author (author), Simek, Jan William, contributor (contributor)
Formato:	Libro electrónico
Idioma:	Inglés
Publicado:	Harlow, England : Pearson [2017]
Edición:	Ninth, global edition
Colección:	Always learning.
Materias:	Chemistry, Organic > Textbooks.
Ver en Biblioteca Universitat Ramon Llull:	https://discovery.url.edu/permalink/34CSUC_URL/1im36ta/alma991009633339306719

Tabla de Contenidos:

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.

Organic chemistry

Ejemplares similares