Organic Chemistry: A Guided Inquiry

Front Cover......Page 1
Title Page......Page 2
Copyright......Page 3
Contents......Page 14
Intro: Organic Chemistry: a Guided Inquiry......Page 18
1 Bond Angles and Shape......Page 25
2 Lewis Structures......Page 33
3 Electron Orbitals......Page 42
Part A: Boiling a Liquid to Form a Gas......Page 52
Part B: H[sup(+)] Transfer Reactions......Page 57
Part C: Acid-Base Reactions & pK[sub(a)]......Page 62
Part A: Drawing Resonance Structures......Page 74
Part B: Resonance Stabilization......Page 79
NW1 Nomenclature Worksheet 1: Naming Alkanes & Cycloalkanes......Page 90
Part A: Conformers of Alkanes......Page 96
Part B: Constitutional Isomers......Page 101
Part C: Alkene Stereoisomers (E/Z & trans/cis)......Page 105
Part A: Cis and Trans Rings......Page 115
Part B: Cyclohexane Chair Conformation......Page 118
NW2 Nomenclature Worksheet 2: Intro to Naming Functional Groups......Page 126
Part A: Addition of H—X to a π Bond......Page 132
Part B: Hydration = Addition of H[sub(2)]O to a π Bond......Page 137
Part A: Bromonium Ion......Page 148
Part B: Epoxides......Page 151
Part A1: Hydroboration/Oxidation......Page 157
Part A2: Catalytic Hydrogenation......Page 159
Part B: Other Oxidation Reactions......Page 161
11 Addition to Alkynes......Page 169
Part A: Chirality......Page 176
Part B: Absolute Configuration......Page 182
Part A: One-step Nucleophilic Substitution......Page 191
Part B: Using pK[sub(a)] to Predict S[sub(N)]2 Reaction Outcomes......Page 195
Part C: Substitution at 2° and 3° Electrophilic Carbons......Page 200
Part D: Factors Affecting S[sub(N)]1 vs. S[sub(N)]2......Page 205
Part A: Two-Step Elimination (E1)......Page 218
Part B: One-Step Elimination (E2)......Page 223
Part C: Stereochemistry of E2 Reactions......Page 229
Part A: Radical Halogenation of Alkanes......Page 242
Part B: Anti-Markovnikov Addition of HBr to a π Bond......Page 248
Part A: Retrosynthesis......Page 256
Part B: Lithium and Grignard Reagents......Page 261
Part C: Lithium Dialkyl Cuprate Reagents......Page 266
L1 Infrared Spectroscopy......Page 278
L2 Mass Spectrometry......Page 287
L3 Carbon ([sup(13)]C) NMR Spectroscopy......Page 301
L4 Proton ([sup(1)]H) NMR Spectroscopy......Page 314
17 Conjugation and Molecular Orbital (MO) Theory......Page 329
Part A: Aromaticity......Page 342
Part B: Molecular Orbital Explanation for Aromaticity......Page 347
NW3 Nomenclature Worksheet 3: Benzene Derivatives......Page 355
Part A: Electrophilic Aromatic Substitution (EAS)......Page 358
Part B: Directing Effects of Electron Donating Groups......Page 362
Part C: Resonance-Withdrawing and Donating Groups......Page 367
Part D: Friedel-Crafts (Special considerations)......Page 371
Part E: Competing Effects & Multi-substituent Rings......Page 375
20 Acidity and pK[sub(a)] of Phenols......Page 391
21 NAS: Nucleophilic Aromatic Substitution......Page 401
22 Synthesis Workshop 2......Page 410
NW4 Nomenclature Worksheet 4: Carbonyl Compounds......Page 416
Part A: Nucleophilic Addition to a Carbonyl (C=O)......Page 424
Part B: Nucleophilic Addition-Elimination......Page 429
Part C: Cyclic Acetal Protecting Groups......Page 433
Part D: Addition to α,β-Unsaturated Carbonyls......Page 437
Part A: Carboxylic Acids, Esters and Amides......Page 451
Part B: Acid Halides & Acid Anhydrides......Page 455
25 Enolate & Enol Nucleophiles......Page 467
Part A: Base-Catalyzed Aldol Reactions......Page 476
Part B: Controlling Product Formation in Aldols......Page 481
Part C: Claisen and Michael Reactions......Page 485
27 Amines......Page 498
Summary of Synthetic Transformations......Page 505
Index......Page 520
Table of pK[sub(a)] Values by Structure......Page 526