The Language of Organic Chemistry
Table of Contents
Chapter 1, Getting Ready for Reactions 1
About the Atom 1
Resonance Structures 2
The Curved Arrow 2
Guide for drawing resonance structures 3
Resonance Structures 3
Anion Resonance structures 3
Cation Resonance Structures 4
Neutral Resonance Structures, with NBE 5
Neutral Resonance Structures, w/o NBE 6
Chapter 2, Acid-Base Chemistry 8
Bronsted-Lowrey Acids and Bases 8
Lewis acids and bases 13
Chapter 3, Substitution Reactions 14
SN2 Substitution Reactions 14
SN1 Substitution Reactions 17
Chapter 4, Elimination Reactions 18
Bromobutane Elimination 18
Other Elimination Reactions 19
Acetylene Formation 20
Hofmann Elimination 21
Cope Elimination 21
Chapter 5, Electrophilic Add. to Alkenes and Alkynes 22
Addition of HX and H2O to Alkenes 22
Bromination 25
Oxymercuration 26
Hydroboration-oxidation of Alkene 27
Carbon-Carbon Triple Bond Electrophilic Reactions
Add. to an Internal Acetylene 28
Add. to a Terminal Acetylene 29
Disiamylborane Hydroboration-Oxid. of Acetylene 30
Chapter 6, Rearrangement Reactions 31
Pinacol Rearrangement 31
Baeyer-Villiger Oxidation 31
Benzilic Acid Rearrangement 32
Dakin Reaction 32
Acetone from Cumene 33
Chapter 7, Electrocyclic reactions 34
Diels Alder Reactions 34
Other Electrocyclic Reactions 37
Chapter 8, Carbonyl Add. Reactions 38
Grignard Add. to a Carbonyl Group 38
Alkyllithium Add. to a Carbonyl Group 38
Wittig Reaction 39
Addition-Elimination Reactions 40
Ketal Formation and Hydrolysis 40
Oxime Formation 41
Add. of Cyanide to a Carbonyl Group 41
Rxns of Acyl Chlorides, Anhydrides, Esters, and Amides 42
Esters f Acid Chlorides or Anhydrides 42
Amides f Acid Chlorides or Anhydrides 43
Ester f Acid with Acid Catalysis (Fischer Esterification) 44
Acid Catalyzed Hydrolysis of an Ester 44
Base Catalyzed Hydrol. of Ester (Saponification) 45
Hydrolysis of an Amide 45
Grignard Add. to an Ester 46
Add. to a Nitrile 47
Chapter 9, Reactions of Enols and Enolates 49
Aldol Reaction 49
Claisen Condensation 51
Acetoacetate Synthesis 52
Halogenation of Carbonyl Compounds 53
Michael Add. or 1,4-Conjugate Add. Rxn 54
Enamine Alkylation 55
Chapter 10, Dehydration Agents 56
Thionyl Chloride Reaction with an Alcohol 56
Rxn of Toluenesulfonyl Chloride with an Alcohol. 56
Rxn of Phosphorus Tribromide with an Alcohol 57
Conversion of an Amide to a Nitrile with Acetic Anhydride 57
Rxn of Carboxylic Acid w/ Thionyl Chloride 58
Rxn of Carboxylic Acid w/ Thionyl Chloride/DMF Catalyst 58
Chapter 11, Reduction Reactions 59
Sodium Borohydride Reductions 59
Lithium Aluminum Hydride Reductions 60
Reductive Amination 62
DIBAH Reduction of an Ester 63
Wolff Kischner reduction 63
Reduction of alkyne with sodium ammonia 64
Catalytic Reduction of Nitrobenzene 64
Chapter 12, Oxidation reactions 65
General form for oxidation 65
Chromic Acid Oxidation of 1-Butanol 65
Pyridinium Chlorochromate Oxidation 66
Tollens Oxidation 66
Hypochlorite Oxidation 66
Swern Oxidation 67
Ozone Oxidation 68
Osmium Tetroxide, Potassium Permanganate, and Periodate Oxidations 69
Chapter 13, Organometallic Reactions 70
Acyclic Heck Reaction 70
Cyclic Heck Reaction 71
Catalytic Reduction of an Alkene 72
Gilman Reagent 72
Chapter 14, Aromatic Substitution Reactions 73
Electrophilic Aromatic Substitution 73
Nucleophilic Aromatic Substitution 76
Benzyne Reaction 76
Diazonium Chemistry 77
Chapter 15, Carbene and Nitrene Reactions 78
Carbene Reactions 78
Carbene Addition 78
Curtius Rearrangement 79
Hoffmann Rearrangement 80
Chapter 16, Radical Reactions 81
Free Radical Bromination (or Chlorination) Rxn 81
Allylic Bromination with NBS 82
Radical Add. of Hydrogen Bromide 83
Notes 84
Common Compounds and Abbreviations 84C