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Tables of Contents for The Art of Writing Reasonable Organic Reaction Mechanisms
Chapter/Section Title
Page #
Page Count
Preface to the Student
v
 
Preface to the Instructor
ix
 
The Basics
1
49
Structure and Stability of Organic Compounds
1
15
Conventions of Drawing Structures; Grossman's Rule
1
2
Lewis Structures; Resonance Structures
3
6
Molecular Shape; Hybridization
9
4
Aromaticity
13
3
Brønsted Acidity and Basicity
16
4
pKa Values
16
3
Tautomerism
19
1
Kinetics and Thermodynamics
20
2
Getting Started in Drawing a Mechanism
22
3
Classes of Overall Transformations
25
1
Classes of Mechanisms
26
16
Polar Mechanisms
27
11
Free-Radical Mechanisms
38
3
Pericyclic Mechanisms
41
1
Transition-Metal-Catalyzed and -Mediated Mechanisms
42
1
Summary
42
8
Problems
43
7
Polar Reactions under Basic Conditions
50
55
Substitution and Elimination at C(sp3)--X σ Bonds, Part I
50
8
Substitution by the SN2 Mechanism
51
2
β-Elimination by the E2 and Elcb Mechanisms
53
3
Predicting Substitution vs. Elimination
56
2
Addition of Nucleophiles to Electrophilic π Bonds
58
11
Addition to Carbonyl Compounds
58
9
Conjugate Addition; The Michael Reaction
67
2
Substitution at C(sp2)--X σ Bonds
69
11
Substitution at Carbonyl C
69
5
Substitution at Alkenyl and Aryl C
74
4
Metal Insertion; Halogen--Metal Exchange
78
2
Substitution and Elimination at C(sp3)--X σ Bonds, Part II
80
7
Substitution by the SRN1 Mechanism
80
1
Substitution by the Elimination--Addition Mechanism
81
1
Substitution by the One-Electron Transfer Mechanism
82
1
Metal Insertion; Halogen--Metal Exchange
83
1
β-Elimination; Generation and Reactions of Carbenes
84
3
Base-Promoted Rearrangements
87
5
Migration from C to C
88
2
Migration from C to O or N
90
1
Migration from B to C or O
91
1
Two Multistep Reactions
92
3
The Swern Oxidation
92
2
The Mitsunobu Reaction
94
1
Summary
95
10
Problems
97
8
Polar Reactions Under Acidic Conditions
105
43
Carbocations
105
12
Carbocation Stability
106
3
Carbocation Generation; The Role of Protonation
109
3
Typical Reactions of Carbocations; Rearrangements
112
5
Substitution and β-Elimination Reactions at C(sp3)--X
117
5
Substitution by the SN1 and SN2 Mechanisms
117
3
β-Elimination by the E1 Mechanism
120
2
Predicting Substitution vs. Elimination
122
1
Electrophilic Addition to Nucleophilic C=C π Bonds
122
3
Substitution at Nucleophilic C=C π Bonds
125
7
Electrophilic Aromatic Substitution
125
4
Aromatic Substitution of Anilines via Diazonium Salts
129
2
Electrophilic Aliphatic Substitution
131
1
Nucleophilic Addition to and Substitution at Electrophilic π Bonds
132
8
Heteroatom Nucleophiles
132
4
Carbon Nucleophiles
136
4
Summary
140
8
Problems
141
7
Pericyclic Reactions
148
76
Introduction
148
8
Classes of Pericyclic Reactions
148
6
Polyene MOs
154
2
Electrocyclic Reactions
156
14
Typical Reactions
156
7
Stereospecificity
163
5
Stereoselectivity
168
2
Cycloadditions
170
25
Typical Reactions
170
13
Regioselectivity
183
1
Stereospecificity
184
7
Stereoselectivity
191
4
Sigmatropic Rearrangements
195
15
Typical Reactions
195
6
Stereospecificity
201
5
Stereoselectivity
206
4
Ene Reactions
210
3
Summary
213
11
Problems
215
9
Free-Radical Reactions
224
46
Free Radicals
224
15
Stability
224
3
Generation from Closed-Shell Species
227
5
Typical Reactions
232
6
Chain vs. Nonchain Mechanisms
238
1
Chain Free-Radical Reactions
239
13
Substitution Reactions
239
5
Addition and Fragmentation Reactions
244
8
Nonchain Free-Radical Reactions
252
9
Photochemical Reactions
252
2
Reductions and Oxidations with Metals
254
7
Cycloaromatizations
261
1
Miscellaneous Radical Reactions
261
3
1,2-Anionic Rearrangements; Lone-Pair Inversion
261
1
Triplet Carbenes and Nitrenes
262
2
Summary
264
6
Problems
264
6
Transition-Metal-Mediated and -Catalyzed Reactions
270
64
Introduction to the Chemistry of Transition Metals
270
13
Conventions of Drawing Structures
270
1
Counting Electrons
271
5
Typical Reactions
276
6
Stoichiometric vs. Catalytic Mechanisms
282
1
Addition Reactions
283
26
Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh)
283
3
Hydroformylation (Co, Rh)
286
1
Hydrozirconation (Zr)
287
1
Alkene Polymerization (Ti, Zr, Sc, and others)
288
2
Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti)
290
2
Dihydroxylation and Aminohydroxylation of Alkenes (Os)
292
2
Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd)
294
3
Conjugate Addition Reactions (Cu)
297
1
Reductive Coupling Reactions (Ti, Zr)
297
4
Pauson-Khand Reaction (Co)
301
2
Dotz Reaction (Cr)
303
3
Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh)
306
3
Substitution Reactions
309
14
Hydrogenolysis (Pd)
309
2
Carbonylation of Alkyl Halides (Pd, Rh)
311
2
Heck Reaction (Pd)
313
1
Coupling Reactions Between Nucleophiles and C(sp2)--X: Kumada, Stille, Suzuki, Negishi, Buchwald--Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu)
314
4
Allylic Substitution (Pd)
318
1
Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation
319
2
Tebbe Reaction (Ti)
321
1
Propargyl Substitution in Co--Alkyne Complexes
322
1
Rearrangement Reactions
323
3
Alkene Isomerization (Rh)
323
1
Olefin and Alkyne Metathesis (Ru, W, Mo, Ti)
323
3
Elimination Reactions
326
1
Oxidation of Alcohols (Cr, Ru)
326
1
Decarbonylation of Aldehydes (Rh)
326
1
Summary
327
7
Problems
328
6
Mixed-Mechanism Problems
334
5
A Final Word
339
2
Index
341