Organic Chemistry I As a Second Language: First Semester Topics, 3rd Edition
ISBN: 9781118010402 | 111801040X
Edition: 3rdFormat: Paperback
Publisher: Wiley
Pub. Date: 7/1/2011
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| Bond-Line Drawings | p. 1 |
| How to Read Bond-Line Drawings | p. 1 |
| How to Draw Bond-Line Drawings | p. 5 |
| Mistakes to Avoid | p. 7 |
| More Exercises | p. 7 |
| Identifying Formal Charges | p. 10 |
| Finding Lone Pairs That Are Not Drawn | p. 14 |
| Resonance | p. 20 |
| What Is Resonance? | p. 20 |
| Curved Arrows: The Tools for Drawing Resonance Struct... MORE | p. 21 |
| The Two Commandments | p. 24 |
| Drawing Good Arrows | p. 27 |
| Formal Charges in Resonance Structures | p. 29 |
| Drawing Resonance Structures-Step by Step | p. 33 |
| Drawing Resonance Structures-By Recognizing Patterns | p. 38 |
| A Lone Pair Next to a Pi Bond | p. 38 |
| A Lone Pair Next to a Positive Charge | p. 41 |
| A Pi Bond Next to a Positive Charge | p. 43 |
| A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.) | p. 44 |
| Pi Bonds Going All the Way Around a Ring | p. 45 |
| Assessing the Relative Importance of Resonance Structures | p. 47 |
| Acid-Base Reactions | p. 53 |
| Factor 1-What Atom Is the Charge on? | p. 54 |
| Factor 2-Resonance | p. 57 |
| Factor 3-Induction | p. 61 |
| Factor 4-Orbitals | p. 64 |
| Ranking the Four Factors | p. 65 |
| Quantitative Measurement (pKa values) | p. 69 |
| Predicting the Position of Equilibrium | p. 70 |
| Showing a Mechanism | p. 71 |
| Geometry | p. 74 |
| Orbitals and Hybridization States | p. 74 |
| Geometry | p. 78 |
| Lone Pairs | p. 81 |
| Nomenclature | p. 83 |
| Functional Group | p. 84 |
| Unsaturation | p. 86 |
| Naming the Parent Chain | p. 88 |
| Naming Substituents | p. 90 |
| Stereoisomerism | p. 94 |
| Numbering | p. 97 |
| Common Names | p. 102 |
| Going from a Name to a Structure | p. 103 |
| Conformations | p. 104 |
| How to Draw a Newman Projection | p. 105 |
| Ranking the Stability of Newman Projections | p. 109 |
| Drawing Chair Conformations | p. 113 |
| Placing Groups on the Chair | p. 116 |
| Ring Flipping | p. 121 |
| Comparing the Stability of Chairs | p. 127 |
| Don't Be Confused by the Nomenclature | p. 131 |
| Configurations | p. 132 |
| Locating Stereocenters | p. 133 |
| Determining the Configuration of a Stereocenter | p. 136 |
| Nomenclature | p. 144 |
| Drawing Enantiomers | p. 149 |
| Diastereomers | p. 154 |
| Meso Compounds | p. 155 |
| Drawing Fischer Projections | p. 158 |
| Optical Activity | p. 163 |
| Mechanisms | p. 165 |
| Curved Arrows | p. 166 |
| Arrow Pushing | p. 171 |
| Drawing Intermediates | p. 173 |
| Nucleophiles and Electrophiles | p. 176 |
| Bases Versus Nucleophiles | p. 177 |
| The Regiochemistry Is Contained Within the Mechanism | p. 180 |
| The Stereochemistry Is Contained Within the Mechanism | p. 183 |
| A List of Mechanisms | p. 188 |
| Substitution Reactions | p. 209 |
| The Mechanisms | p. 209 |
| Factor 1-The Electrophile (Substrate) | p. 212 |
| Factor 2-The Nucleophile | p. 215 |
| Factor 3-The Leaving Group | p. 217 |
| Factor 4-The Solvent | p. 220 |
| Using All Four Factors | p. 223 |
| Substitution Reactions Teach Us Some Important Lessons | p. 224 |
| Elimination Reactions | p. 226 |
| The E2 Mechanism | p. 226 |
| The Regiochemical Outcome of an E2 Reaction | p. 227 |
| The Stereochemical Outcome of an E2 Reaction | p. 229 |
| The E1 Mechanism | p. 232 |
| The Regiochemical Outcome of an E1 Reaction | p. 233 |
| The Stereochemical Outcome of an E1 Reaction | p. 234 |
| Substitution vs. Elimination | p. 234 |
| Determining the Function of the Reagent | p. 235 |
| Identifying the Mechanism(s) | p. 238 |
| Predicting the Products | p. 241 |
| Addition Reactions | p. 245 |
| Terminology Describing Regiochemistry | p. 245 |
| Terminology Describing Stereochemistry | p. 247 |
| Adding H and H | p. 256 |
| Adding H and X, Markovnikov | p. 259 |
| Adding H and Br, Anti-Markovnikov | p. 266 |
| Adding H and OH, Markovnikov | p. 271 |
| Adding H and OH, Anti-Markovnikov | p. 275 |
| Synthesis Techniques | p. 279 |
| Adding Br and Br; Adding Br and OH | p. 287 |
| Adding OH and OH, Anti | p. 293 |
| Adding OH and OH, Syn | p. 296 |
| Oxidative Cleavage of an Alkene | p. 298 |
| Alcohols | p. 302 |
| Naming and Designating Alcohols | p. 302 |
| Predicting Solubility of Alcohols | p. 303 |
| Predicting Relative Acidity of Alcohols | p. 306 |
| Preparing Alcohols: A Review | p. 309 |
| Preparing Alcohols via Reduction | p. 310 |
| Preparing Alcohols via Grignard Reactions | p. 317 |
| Summary of Methods for Preparing Alcohols | p. 322 |
| Reactions of Alcohols: Substitution and Elimination | p. 323 |
| Reactions of Alcohols: Oxidation | p. 327 |
| Converting an Alcohol into an Ether | p. 329 |
| Synthesis | p. 332 |
| One-step Syntheses | p. 333 |
| Multistep Syntheses | p. 345 |
| Retrosynthetic Analysis | p. 346 |
| Creating Your Own Problems | p. 347 |
| Answer Key | p. 349 |
| Index | p. 375 |
| Table of Contents provided by Ingram. All Rights Reserved. |
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