How to succeed in organic chemistry

by Mark Elliott

Overview

'How to succeed in organic chemistry' gives the reader a solid understanding of the principles of organic reaction mechanisms, such that they can draw structures, stereoisomers and reaction mechanisms with confidence. Throughout, the author speaks the language of students to build their confidence and interest.

At heart, the book promotes active learning to ensure the necessary skills become so ingrained that they become something students simply cannot forget, and do not need to revise. As such, the book structures learning so that the reader encounters the right things at the right time, helping to 'internalise' key concepts.

Concepts, explanations and examples are presented in short, easy-to-read chapters, each of which explores one of a number of themes, including 'Basics', 'Habits', 'Common error', 'Reaction detail', and 'Practice'.

The text is accompanied by over 40 videos, in which the author discusses the solutions to problems posed in the text, thereby giving even more support and encouragement to the learner.

Product Details

ISBN-13:	9780198851295
Publisher:	Oxford University Press
Publication date:	03/20/2020
Pages:	520
Product dimensions:	9.50(w) x 6.80(h) x 0.90(d)

About the Author

Mark Elliott, Senior Lecturer in Organic Chemistry and Deputy Director of Learning and Teaching, School of Chemistry, Cardiff University

Dr Mark Elliott is Senior Lecturer in Organic Chemistry and Deputy Director of Learning and Teaching in the Department of Chemistry at Cardiff University. His research interests lie in the development of new synthetic methodology, and its application to target synthesis. He teaches organic chemistry at all levels of the undergraduate curriculum.

Table of Contents

Foreword xi

Inspiration xv

Acknowledgements xvii

Additional Resources xix

Style and Substance xxi

Section 1 Laying the Foundations 1

Basics 1 Structures of Organic Compounds 3

Habit 1 Always Draw Structures with Realistic Geometry 11

Basics 2 Functional Groups and 'R' Groups 13

Basics 3 Naming Organic Compounds 19

Practice 1 Drawing Structures from Chemical Names 26

Basics 4 Isomerism in Organic Chemistry-Constitutional Isomers 29

Practice 2 Constitutional Isomers and Chemical Names 31

Habit 2 Identifying When a Formula is Possible 33

Practice 3 Double Bond Equivalents 36

Common Error 1 Formulae, Functional Groups, and Double Bond Equivalents 39

Habit 3 Ignore What Doesn't Change 42

Basics 5 Electronegativity, Bond Polarization, and Inductive Effects 44

Practice 4 Bond Polarization and Electronegativity 46

Basils 6 Bonding in Organic Compounds 48

Practice 5 Hybridization 59

Basics 7 Bonding and Antibonding Orbitals 62

Basics 8 Introduction to Curly Arrows 65

Fundamental Reaction Type 1 Nucleophilic Substitution at Saturated Carbon 72

Practice 6 Electronegativity in Context 76

Fundamental Reaction Type 2 Elimination Reactions 78

Section 2 Building on the Foundations 83

Basics 9 Breaking Bonds-Linking Curly Arrows and Molecular Orbitals 85

Common Error 2 Curly Arrows 93

Basics 10 Conjugation and Resonance 95

Basics 11 Thermodynamic Definitions 105

Basics 12 Bond Dissociation Energy 108

Basics 13 Calculating Enthalpy of Reaction from Bond Dissociation Energies 111

Perspective 1 A Closer Look at Bond Dissociation Energies 114

Practice 7 Calculating Enthalpy of Reaction from Bond Dissociation Energy 118

Basics 14 Energetics and Reaction Profiles 123

Basics 15 How Fast Are Reactions? 128

Basics 16 Introduction to Carbocations, Carbanions, and Free-Radicals 131

Basks 17 Carbocations 2-More Factors Affecting Stability 140

Basics 18 Carbanions 2-Stability and pK_a 148

Perspective 2 A Scale for Carbocation Stability 159

Common Error 3 Methyl Groups are Electron-Releasing 167

Practice 8 Drawing Resonance Forms for Carbocations and Carbanions 170

Common Error 4 Resonance 176

Basics 19 The Hammond Postulate 179

Basics 20 Conjugation and Stability-The Evidence 183

Common Error 5 Carbocations and Carbanions 187

Basics 21 Reactivity of Conjugated Systems 189

Basics 22 Acid Catalysis in Organic Reactions Part 1 191

Reaction Detail 1 Nucleophilic Substitution at Saturated Carbon 196

Basics 23 What Defines a Transition State? 209

Perspective 3 Bonding Beyond Hybridization 212

Fundamental Knowledge Recap 1 Bond Lengths and Strengths 221

Fundamental Knowledge Recap 2 pK_a 222

Section 3 A Focus on Shape 223

Habit 4 Representing Stereochemistry-Flying Wedge and Newman Projections 225

Basics 24 Isomerism in Organic Chemistry-Configurational Isomers 228

Habit 5 Getting Used to Drawing Stereoisomers 232

Practice 9 Getting Used to Stereoisomers 240

Habit 6 Assignment of Stereochemistry-The Cahn-Ingold-Prelog Rules 243

Practice 10 Assigning Stereochemistry 254

Habit 7 Stereoisomers with Symmetry 256

Basics 25 Properties of Stereoisomers 260

Reaction Datail 2 Stereochemical Aspects of Substitution Reactions 263

Common Error 6 Substitution Reactions 271

Reaction Detail 3 Substitution with Retention of Configuration 273

Common Error 7 Stereochemical Errors 275

Section 4 Types of Selectivity 279

Basics 26 Selectivity in Organic Chemistry-Chemoselectivity 281

Basics 27 Selectivity in Organic Chemistry-Regioselectivity 282

Basics 28 Selectivity in Organic Chemistry-Stereoselectivity 283

Basics 29 Stereochemical Definitions Relating to Reactions 290

Section 5 Bonds Can Rotate 293

Basics 30 Isomerism in Organic Chemistry-Conformational Isomers 295

Practice 11 Conformational Analysis 300

Applications 1 Conformational Isomers 2 303

Applications 2 S_N2 Substitution Reactions Forming Three-Membered Rings 308

Basics 31 Introduction to Cyclohexanes 315

Practice 12 Drawing Cyclohexanes 326

Applications 3 Substitution Reactions of Cyclohexanes 329

Basics 32 Quantifying Conformers of Cyclohexanes 335

Basics 33 More Conformers of Cyclohexanes and Related Compounds 342

Practice 13 Drawing More Complex Cyclohexanes 347

Common Error 8 Cyclohexanes 350

Section 6 Eliminating the Learning 353

Reaction Detail 4 Elimination Reactions 355

Perspective 4 A Continuum of Mechanisms 364

Basics 34 More Substituted Alkenes Are More Stable 368

Basics 35 Enthalpy Changes for Reactions Involving Anionic Species 372

Applications 4 Stereochemistry of Elimination Reactions 375

Basics 36 Stereospecificity 381

Applications 5 Elimination Reactions of Cyclohexanes 383

Common Error 9 Elimination Reactions 390

Reaction Detail 5 Allylic Substitution 391

Section 7 Building Skills 397

Worked Problem 1 Curly Arrows and Reaction Profiles 399

Worked Problem 2 Competing S_N1 Substitution and E1 Elimination 403

Worked Problem 3 Competing S_N2 Substitution and E2 Elimination 406

Worked Problem 4 Acid Catalysis in Organic Reactions Part 2 410

Worked Problem 5 Epoxide Opening Reactions 414

Worked Problem 6 Is cis-Cyclohexane-1,2-diol Really Achiral? 417

Worked Problem 7 The Fürst-Plattner Rule 419

Worked Problem 8 S_N2' Stereochemistry and Conformations 423

Worked Problem 9 Complex Substitution Stereochemistry 426

Worked Problem 10 Cyclization Reactions 430

Solution to Problem 1 Curly Arrows and Reaction Profiles 434

Solution to Problem 2 Competing S_N1 Substitution and E1 Elimination 438

Solution to Problem 3 Competing S_N2 Substitution and E2 Elimination 444

Solution to Problem 4 Acid Catalysis in Organic Reactions Part 2 449

Solution to Problem 5 Epoxide Opening Reactions 454

Solution to Problem 6 Is cis-Cyclohexane-1,2-diol Really Achiral? 457

Solution to Problem 7 The Fürst-Plattner Rule 461

Solution to Problem 8 S_N2' Stereochemistry and Conformations 470

Solution to Problem 9 Complex Substitution Stereochemistry 476

Solution to Problem 10 Cyclization Reactions 482

Afterword 487

Index 489