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A Guide to Organic Chemistry Mechanisms
Table of Contents
Acknowledgements  -  iii
To the Instructor  -  iv
To the Student  -  iv
Table of Contents  -  v
Index  -  vii
Preface
About the Book  -  xiii
The Curved Arrow  -  xiv
Rules for Pushing Electrons  -  xiv
1  -  Getting Ready for Reactions
About the Atom  -  1
Guide to Drawing Resonance Structures  -  2
Resonance Structures of Anions  -  2
Resonance Structures of Cations  -  3
Resonance Structures of Neutral Compounds with Non-Bonded Electrons  -  4
Resonance Structures of Neutral Compounds without Non-Bonded Electrons  -  5
Resonance Structures of Radicals  -  6
2  -  Acid-Base Chemistry
Bronsted-Lowrey Acids and Bases  -  7
Lewis Acids and Bases  -  11
3  -  Substitution Reactions
SN2 Substitution Reactions  -  12
SN1 Substitution Reactions  -  16
4  -  Elimination Reactions
Alkene Formation  -  18
Acetylene Formation  -  23
5  -  Electrophilic Addition to Alkenes and Alkynes
Carbon-Carbon Double Bond Reactions
Addition of HX and H2O to Alkenes  -  24
Bromination  -  27
Oxymercuration  -  28
Hydroboration-Oxidation of Alkene  -  29
Carbon-Carbon Triple Bond Reactions
Addition to an Internal Acetylene  -  31
Addition to a Terminal Acetylene  -  32
Disiamylborane Hydroboration-Oxidation of an Acetylene  -  33
6  -  Rearrangement Reactions
Baeyer-Villiger Oxidation  -  34
Pinacol Rearrangement  -  36
Benzilic Acid Rearrangement  -  36
Dakin Reaction  -  37
Acetone from Cumene  -  37
7  -  Electrocyclic Reactions
Diels Alder Reactions  -  38
Other Electrocyclic Reactions  -  41
8  -  Carbonyl Addition and Addition-Elimination Reactions
Grignard Addition to a Carbonyl Group -  42
Alkyllithium Addition to a Carbonyl Group  -  42
Wittig Reaction  -  43
Addition-Elimination Reactions (Reversible Additions)  -  44
Ketal Formation and Hydrolysis  -  44
Oxime Formation  -  45
Other Additions to a Carbonyl Group  -  45
Reactions of Acyl Chlorides, Anhydrides, Esters, and Amides  -  46
Esters from Acid Chlorides or Anhydrides  -  46
Amides from Acid Chlorides or Anhydrides  -  47
Ester from Acid with Mineral Acid Catalysis
(Fischer Esterification)  -  48
Acid Catalyzed Hydrolysis of an Ester  -  48
Base Hydrolysis of an Ester (Saponification) - 49
Hydrolysis of an Amide  -  49
Reactions of Esters  -  50
Reactions of Nitriles  -  51
Miscellaneous, Ester with Diazomethane  -  52
9  -  Reactions of Enols and Enolates
Aldol Reaction  -  53
Claisen Condensation  -  55
Acetoacetate Synthesis  -  56
Enolate Alkylation Reactions  -  57
Halogenation of Carbonyl Compounds  -  58
Michael or 1,4-Conjugate Addition Reaction-59
Enamine Alkylation  -  60
10  -  Dehydration/Halogenation Agents
Carboxylic Acid with Thionyl Chloride  -  62
Alcohol with a Phosphorus Reagent  -  63
11  -  Reduction Reactions
Sodium Borohydride Reductions  -  64
Lithium Aluminum Hydride Reductions  -  65
Reductive Amination  -  67
Diisobutylaluminum Hydride Reduction  -  68
Reduction of Alkyne with Sodium/NH3  -  68
Wolff Kischner Reduction  -  69
Catalytic Reduction of Nitrobenzene  -  69
12  -  Oxidation-Reactions
General Form For Oxidations  -  70
Chromic Acid Oxidation  -  70
PCC, Tollens, Hypochlorite, and Sulfonium Based Oxidations  -  71
Peracid Epoxidation, MCPBA  -  71
Ozone Oxidation  -  73
Osmium Tetroxide, Permanganate, and Periodate Oxidations  -  74
13  -  Organometallic Reactions
Acyclic Heck Reaction  -  75
Cyclic Heck Reaction  -  76
Catalytic Reduction of an Alkene  -  77
Gilman Reagent  -  77
14  -  Aromatic Substitution Reactions
Electrophilic Aromatic Substitution, of Benzene  -  78
Electrophilic Aromatic Substitution of Substituted Aromatic Compounds  -  79
Nucleophilic Aromatic Substitution  -  81
Benzyne Reaction  -  81
Diazonium Chemistry  -  82
15  -  Carbene and Nitrene Reactions
Carbene Reactions  -  83
Curtius Rearrangement  -  84
Hoffmann Rearrangement  -  85
16  -  Radical Reactions
Free Radical Bromination Reaction  -  86
Allylic Bromination with NBS  -  87
Radical Addition of Hydrogen Bromide -  88
Benzylic Bromination with NBS  -  89
Notes
Notes to Specific Reactions  -  Notes 1-26