Organic Chemistry I As a Second Language: First Semester Topics, 3rd Edition

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  • Edition: 3rd
  • Format: Paperback
  • Copyright: 2011-07-01
  • Publisher: Wiley
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Readers continue to turn to Klein because it enables them to better understand fundamental principles, solve problems, and focus on what they need to know to succeed. This edition explores the major principles in the field and explains why they are relevant. It is written in a way that clearly shows the patterns in organic chemistry so that readers can gain a deeper conceptual understanding of the material. Topics are presented clearly in an accessible writing style along with numerous of hands-on problem solving exercises.

Table of Contents

Bond-Line Drawingsp. 1
How to Read Bond-Line Drawingsp. 1
How to Draw Bond-Line Drawingsp. 5
Mistakes to Avoidp. 7
More Exercisesp. 7
Identifying Formal Chargesp. 10
Finding Lone Pairs That Are Not Drawnp. 14
Resonancep. 20
What Is Resonance?p. 20
Curved Arrows: The Tools for Drawing Resonance Structuresp. 21
The Two Commandmentsp. 24
Drawing Good Arrowsp. 27
Formal Charges in Resonance Structuresp. 29
Drawing Resonance Structures-Step by Stepp. 33
Drawing Resonance Structures-By Recognizing Patternsp. 38
A Lone Pair Next to a Pi Bondp. 38
A Lone Pair Next to a Positive Chargep. 41
A Pi Bond Next to a Positive Chargep. 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 Ringp. 45
Assessing the Relative Importance of Resonance Structuresp. 47
Acid-Base Reactionsp. 53
Factor 1-What Atom Is the Charge on?p. 54
Factor 2-Resonancep. 57
Factor 3-Inductionp. 61
Factor 4-Orbitalsp. 64
Ranking the Four Factorsp. 65
Quantitative Measurement (pKa values)p. 69
Predicting the Position of Equilibriump. 70
Showing a Mechanismp. 71
Geometryp. 74
Orbitals and Hybridization Statesp. 74
Geometryp. 78
Lone Pairsp. 81
Nomenclaturep. 83
Functional Groupp. 84
Unsaturationp. 86
Naming the Parent Chainp. 88
Naming Substituentsp. 90
Stereoisomerismp. 94
Numberingp. 97
Common Namesp. 102
Going from a Name to a Structurep. 103
Conformationsp. 104
How to Draw a Newman Projectionp. 105
Ranking the Stability of Newman Projectionsp. 109
Drawing Chair Conformationsp. 113
Placing Groups on the Chairp. 116
Ring Flippingp. 121
Comparing the Stability of Chairsp. 127
Don't Be Confused by the Nomenclaturep. 131
Configurationsp. 132
Locating Stereocentersp. 133
Determining the Configuration of a Stereocenterp. 136
Nomenclaturep. 144
Drawing Enantiomersp. 149
Diastereomersp. 154
Meso Compoundsp. 155
Drawing Fischer Projectionsp. 158
Optical Activityp. 163
Mechanismsp. 165
Curved Arrowsp. 166
Arrow Pushingp. 171
Drawing Intermediatesp. 173
Nucleophiles and Electrophilesp. 176
Bases Versus Nucleophilesp. 177
The Regiochemistry Is Contained Within the Mechanismp. 180
The Stereochemistry Is Contained Within the Mechanismp. 183
A List of Mechanismsp. 188
Substitution Reactionsp. 209
The Mechanismsp. 209
Factor 1-The Electrophile (Substrate)p. 212
Factor 2-The Nucleophilep. 215
Factor 3-The Leaving Groupp. 217
Factor 4-The Solventp. 220
Using All Four Factorsp. 223
Substitution Reactions Teach Us Some Important Lessonsp. 224
Elimination Reactionsp. 226
The E2 Mechanismp. 226
The Regiochemical Outcome of an E2 Reactionp. 227
The Stereochemical Outcome of an E2 Reactionp. 229
The E1 Mechanismp. 232
The Regiochemical Outcome of an E1 Reactionp. 233
The Stereochemical Outcome of an E1 Reactionp. 234
Substitution vs. Eliminationp. 234
Determining the Function of the Reagentp. 235
Identifying the Mechanism(s)p. 238
Predicting the Productsp. 241
Addition Reactionsp. 245
Terminology Describing Regiochemistryp. 245
Terminology Describing Stereochemistryp. 247
Adding H and Hp. 256
Adding H and X, Markovnikovp. 259
Adding H and Br, Anti-Markovnikovp. 266
Adding H and OH, Markovnikovp. 271
Adding H and OH, Anti-Markovnikovp. 275
Synthesis Techniquesp. 279
Adding Br and Br; Adding Br and OHp. 287
Adding OH and OH, Antip. 293
Adding OH and OH, Synp. 296
Oxidative Cleavage of an Alkenep. 298
Alcoholsp. 302
Naming and Designating Alcoholsp. 302
Predicting Solubility of Alcoholsp. 303
Predicting Relative Acidity of Alcoholsp. 306
Preparing Alcohols: A Reviewp. 309
Preparing Alcohols via Reductionp. 310
Preparing Alcohols via Grignard Reactionsp. 317
Summary of Methods for Preparing Alcoholsp. 322
Reactions of Alcohols: Substitution and Eliminationp. 323
Reactions of Alcohols: Oxidationp. 327
Converting an Alcohol into an Etherp. 329
Synthesisp. 332
One-step Synthesesp. 333
Multistep Synthesesp. 345
Retrosynthetic Analysisp. 346
Creating Your Own Problemsp. 347
Answer Keyp. 349
Indexp. 375
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