Information
Index
A
Acid-Base Chemistry 7-11
acetylide 9
alkoxide 8
amide anion 9
Bronsted-Lowrey 7-10
ester enolate 10
ketone enolate 9
Lewis acids 11
methyl anion 9
Addition to Alkenes and Alkynes 24-33
acetic acid 24
bromine 26, 27, 31
bromine-water 27
HBr 24, 25
HCl 25, 26, 31
hydration. See Addition, water
hydroboration-oxidation 29, 30, 33
oxymercuration-reduction 28
water
mercury 32
mineral acid 24, 32
Aromatic Substitution Reactions 78-82
benzyne reaction 81
diazonium formation 82
diazonium reaction 82
electrophilic aromatic substitution 78-80
bromination 78, 79
chlorination 80
Friedel-Crafts acylation 78, 79
Friedel-Crafts alkylation 78, 80
nitration 79
triflic acid acylation 80
nucleophilic aromatic substitution 81
B
C
Carbene and Nitrene Reactions 83-85
Curtius rearrangement 84
dihalocarbene 83
Hoffmann rearrangement 85
Simmons-Smith addition 83
Carbonyl Addition Rxns 42-52
acid chloride
alcohol 46
amine 47
aldehyde
alkyllithium 42
ester enolate 45
Grignard rgt 42
Wittig rxn 43
Horner-Wadsworth-Emmons 43
amide
acid hydrolysis 50
base hydrolysis 49
anhydride
alcohol 46
amine 47
carboxylic acid
alcohol mineral acid 48
diazomethane 52
ester
amine 50
base hydrolysis 49
mineral acid 48
t-butyl w acid 48
ketone
alkyllithium 42
cyanide 45
Grignard rgt 42
ketal formation 44
oxime 45
reverse cyanide addition 45
nitrile
acid hydrolysis 51
alkyllithium 52
base hydrolysis 51
Carbonyl Enols and Enolates 53-60
aldehyde
aldol condensation 53
mixed or crossed aldol 54
ester
alkylation 57
Claisen condensation 55
mixed Claisen condensation 55
ketoester
Acetoacetate Synthesis 56
dianion alkylation 57
Michael addition 59
retro-Claisen reaction 57
ketone
bromination, alpha 58
Conjugate Addition 59
directed aldol condensation 53
enamine alkylation 60
Halogenation, haloform rxn 58
Mannich reaction 54
mixed Claisen condensation 55
nitrile
alkylation 57
Curved Arrow xiv
D
Dehydration/Halogenation Agents 61-63
alcohol
phosphorous tribromide 63
thionyl chloride 61
tosyl chloride 61
triphenylphosphine, carbon tetrachloride 63
amide
anhydride 61
thionyl chloride 62
carboxylic acid
iminium salt 62
thionyl chloride 62
E
Electrocyclic Reactions 38-41
3+2 cycloaddition 41
Claisen rearrangement 41
Diels-Alder 38-40
reverse Diels-Alder 39
Elimination Reactions 18-23
amide anion 23
amine oxide 22
ammonium salt 22
Cope elimination 22
E1 21
E1cb 20
E2 18-20
ethoxide 18, 19, 20
Hofmann elimination 22
LDA 23
mineral acid 21
selenoxide 22
t-butoxide 18, 19, 20, 23
F
Functional Group Index
By Preparation of x
By Reaction of xi
G-M
N
Named Reagents & Reactions
Arbusov reaction 43
Baeyer-Villiger 34, 35
Trifluoroperacetic acid 35
benzilic acid 36
benzyne reaction 81
Claisen condensation 55
Claisen rearrangement 41
Cope elimination 22
Corey-Kim oxidation 72
Curtius rearrangement 84
Dakin Reaction 37
diazomethane 52
Diels Alder 38
Fischer esterification 48
Friedel-Crafts 78
Gabriel amine synthesis 14
Gilman reagent 77
Grignard reagent 42
haloform reaction 58
Heck reaction 75
Hoffmann rearrangement 85
Hofmann elimination 22
Horner-Wadsworth-Emmons 43
Jones oxidation 70
Mannich reaction 54
Michael addition 59
pinacol 36
saponification 49
Saytzeff 18
Simmons-Smith reagent 83
Swern oxidation 72
Tollens oxidation 71
Wittig reaction 43
Wolff Kischner reduction 69
O
Organometallic Reactions 75-77
catalytic hydrogenation 77
Gilman reagent 77
acid chloride 77
conjugate addition 77
formation 77
Heck reaction 75, 76
Oxidation Reactions 70-74
alcohol
chromic acid oxidation 70
DMSO oxidation (Swern) 72
pyridinium chlorochromate 71
Swern oxidation 72
alkene
osmium tetroxide 74
ozone 73
permanganate 74
diol
Periodate 74
P-Q
R
Radical Reactions
allylic bromination 87
anti-Markovnikov addition 88
benzylic bromination 89
Bromination 86-88
Chlorination 86
Reactant by Type
acid 48, 52, 62, 67
acid anhydride 46-47, 61, 80
acid chloride 46-47, 77, 78, 79, 84
alcohol 12, 16, 17, 21, 61, 63, 71, 72
aldehyde 42, 42, 42, 43, 53, 64, 67, 70, 71
alkane 86, 89
alkene 23, 24-30, 71, 73, 74, 75-77, 83, 87, 88
alkyne 42, 42, 42, 13, 15, 31-33, 42, 68
amide 49, 50, 61, 62, 66, 85
amide anion 81
amine 22, 54, 59, 60, 67, 81
azobisisobutyronitrile 89
diol 74
enolate 15, 15, 53
enone 77
epoxide 15, 15
ester 48-49, 50, 55, 65, 68
ester enolate 14, 45, 55, 57
ether 14, 14
halide 14, 12, 13, 14, 16, 17, 18-21,
23, 43, 56, 57, 75-76, 77, 78, 80
halogenation 26-27, 78-80, 86-89
ketoester 56, 59
ketone 42, 44, 45, 53, 54, 58, 59, 60, 64, 65, 69
methyl vinyl ketone 59
LDA 57
nitric acid 79
nitrile 51, 57
nitro 69
oxidation 34
peracid 34, 35, 71
peroxide 37
phenoxide 14
tosylate 13
triflate 13
Rearrangement 34-36
1,2-cyclohexanediol 36-37
Acetone from Cumene 37
Baeyer-Villiger oxidation
acetophenone 35, 35, 35, 34-35, 35
aldehyde 35, 35, 35, 34, 35
Benzophenone 35, 35, 35, 35
dimethylcyclopentanone 34
Benzilic Acid Rearrangement 36
Dakin Reaction 37
peracid 34-35
Pinacol Rearrangement 36
Reduction Reactions 64-69
borohydride
aldehyde 64
cyclopentanone 64
ketoester 64
reductive amination 67
catalytic reduction
nitro 69
diisobutylaluminum hydride
ester 68
hydrazine
ketone 69
lithium aluminum hydride
amide 66
carboxylic acid 67
ester 65
ketone 65
sodium-ammonia
alkyne 68
Resonance Structures 2-6
S
Substitution Reactions
acetate 12
acetylide 13, 15, 5, 7
alcohol 15
anisole 14
azide 13
bromide 12, 15, 17
chloride 16
cyanide 13, 4
enolate, ester 14
enolate, ketone 15, 15
epoxide 15
ethoxide 14, 12, 14
iodide 12, 14
oxirane 15
phenoxide 14
phthalimide 14
SN1 16-17
SN2 12-14
solvolysis 16, 17
thiocyanate 12
T-Z