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

by David R. Klein

• ISBN13: 9781118010402
• ISBN10: 111801040X
• Edition: 3rd
• Format: Paperback
• Copyright: 2011-07-01
• Publisher: Wiley

Summary

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 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 Structures	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.