Helps develop the skills needed to solve a variety of problem types. Presents the fundamental topics clearly with an informal, friendly tone. Describes the how–to of problem solving, including approaching problems strategically. Discusses the relationship between concepts and puts topics in context. Covers important areas such as resonance, nomenclature, conformations, substitution reactions, synthesis and more. INDICE: CHAPTER 1 BOND–LINE DRAWINGS 1 .1.1 How to Read Bond–Line Drawings 1 .1.2 How to Draw Bond–Line Drawings 5 .1.3 Mistakes to Avoid 7 .1.4 More Exercises 7 .1.5 Identifying Formal Charges 9 .1.6 Finding Lone Pairs that are Not Drawn 13 .CHAPTER 2 RESONANCE 18 .2.1 What is Resonance? 18 .2.2 Curved Arrows: The Tools for Drawing Resonance Structures 19 .2.3 The Two Commandments 21 .2.4 Drawing Good Arrows 24 .2.5 Formal Charges in Resonance Structures 26 .2.6 Drawing Resonance Structures Step by Step 30 .2.7 Drawing Resonance Structures by Recognizing Patterns 34 .2.8 Assessing the Relative Importance of Resonance Structures 43 .CHAPTER 3 ACID BASE REACTIONS 49 .3.1 Factor 1 What Atom is the Charge On? 50 .3.2 Factor 2 Resonance 53 .3.3 Factor 3 Induction 56 .3.4 Factor 4 Orbitals 59 .3.5 Ranking the Four Factors 60 .3.6 Other Factors 63 .3.7 Quantitative Measurement (pKa Values) 64 .3.8 Predicting the Position of Equilibrium 65 .3.9 Showing a Mechanism 66 .CHAPTER 4 GEOMETRY 69 .4.1 Orbitals and Hybridization States 69 .4.2 Geometry 72 .4.3 Lone Pairs 76 .CHAPTER 5 NOMENCLATURE 77 .5.1 Functional Group 78 .5.2 Unsaturation 80 .5.3 Naming the Parent Chain 81 .5.4 Naming Substituents 84 .5.5 Stereoisomerism 88 .5.6 Numbering 90 .5.7 Common Names 95 .5.8 Going from a Name to a Structure 96 .CHAPTER 6 CONFORMATIONS 97 .6.1 How to Draw a Newman Projection 98 .6.2 Ranking the Stability of Newman Projections 102 .6.3 Drawing Chair Conformations 105 .6.4 Placing Groups On the Chair 108 .6.5 Ring Flipping 112 .6.6 Comparing the Stability of Chairs 119 .6.7 Don t Be Confused by the Nomenclature 122 .CHAPTER 7 CONFIGURATIONS 123 .7.1 Locating Stereocenters 123 .7.2 Determining the Configuration of a Stereocenter 126 .7.3 Nomenclature 134 .7.4 Drawing Enantiomers 138 .7.5 Diastereomers 143 .7.6 Meso Compounds 144 .7.7 Drawing Fischer Projections 147 .7.8 Optical Activity 152 .CHAPTER 8 MECHANISMS 154 .8.1 Introduction to Mechanisms 154 .8.2 Nucleophiles and Electrophiles 154 .8.3 Basicity vs. Nucleophilicity 157 .8.4 Arrow–Pushing Patterns for Ionic Mechanisms 159 .8.5 Carbocation Rearrangements 164 .8.6 Information Contained in a Mechanism 169 .CHAPTER 9 SUBSTITUTION REACTIONS 173 .9.1 The Mechanisms 173 .9.2 Factor 1 The Electrophile (Substrate) 175 .9.3 Factor 2 The Nucleophile 178 .9.4 Factor 3 The Leaving Group 180 .9.5 Factor 4 The Solvent 183 .9.6 Using All Four Factors 185 .9.7 Substitution Reactions Teach Us Some Important Lessons 186 .CHAPTER 10 ELIMINATION REACTIONS 188 .10.1 The E2 Mechanism 188 .10.2 The Regiochemical Outcome of an E2 Reaction 189 .10.3 The Stereochemical Outcome of an E2 Reaction 191 .10.4 The E1 Mechanism 194 .10.5 The Regiochemical Outcome of an E1 Reaction 195 .10.6 The Stereochemical Outcome of an E1 Reaction 196 .10.7 Substitution vs. Elimination 196 .10.8 Determining the Function of the Reagent 197 .10.9 Identifying the Mechanism(s) 199 .10.10 Predicting the Products 202 .CHAPTER 11 ADDITION REACTIONS 206 .11.1 Terminology Describing Regiochemistry 206 .11.2 Terminology Describing Stereochemistry 208 .11.3 Adding H and H 216 .11.4 Adding H and X, Markovnikov 219 .11.5 Adding H and Br, Anti–Markovnikov 226 .11.6 Adding H and OH, Markovnikov 230 .11.7 Adding H and OH, Anti–Markovnikov 233 .11.8 Synthesis Techniques 238 .11.9 Adding Br and Br; Adding Br and OH 245 .11.10 Adding OH and OH, ANTI 250 .11.11 Adding OH and OH, SYN 253 .11.12 Oxidative Cleavage of an Alkene 255 .CHAPTER 12 ALKYNES 258 .12.1 Structure and Properties of Alkynes 258 .12.2 Preparation of Alkynes 261 .12.3 Alkylation of Terminal Alkynes 262 .12.4 Reduction of Alkynes 264 .12.5 Hydration of Alkynes 268 .12.6 Keto–Enol Tautomerization 273 .12.7 Ozonolysis of Alkynes 278 .CHAPTER 13 ALCOHOLS 280 .13.1 Naming and Designating Alcohols 280 .13.2 Predicting Solubility of Alcohols 281 .13.3 Predicting Relative Acidity of Alcohols 283 .13.4 Preparing Alcohols: A Review 286 .13.5 Preparing Alcohols via Reduction 287 .13.6 Preparing Alcohols via Grignard Reactions 294 .13.7 Summary of Methods for Preparing Alcohols 298 .13.8 Reactions of Alcohols: Substitution and Elimination 300 .13.9 Reactions of Alcohols: Oxidation 303 .13.10 Converting an Alcohol Into an Ether 305 .CHAPTER 14 ETHERS AND EPOXIDES 308 .14.1 Introduction to Ethers 308 .14.2 Preparation of Ethers 310 .14.3 Reactions of Ethers 313 .14.4 Preparation of Epoxides 314 .14.5 Ring–Opening Reactions of Epoxides 316 .CHAPTER 15 SYNTHESIS 323 .15.1 One–Step Syntheses 324 .15.2 Multistep Syntheses 336 .15.3 Retrosynthetic Analysis 337 .15.4 Creating Your Own Problems 338 .Answer Key 339 .Index 000
- ISBN: 978-1-119-11066-8
- Editorial: John Wiley & Sons
- Encuadernacion: Rústica
- Páginas: 400
- Fecha Publicación: 07/06/2016
- Nº Volúmenes: 1
- Idioma: Inglés