Organic Chemistry -Free Course
Index
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1
1,2-product - IV.2
1,3-diaxial interaction I.16
1,4-product -- IV.2
alpha
alpha-carbon · 386, 387
alpha,beta-Unsaturated Carbonyls · 395, 401, 403, 404, 405
A
acetals · 352
acetoacetic ester synthesis · 397
acetone · 108
acetonitrile · 108
acetophenone · 250
Acetylide Anion · 215
Acid Cleavage of Ethers · 145
Acidity · 246
Acids and Bases · 47
Activating a Poor Leaving Group · 136
Acyclic Diene Metathesis · 325
Acylium · 255
ADMET · 326, 327
alcohols · 282, 283, 329, 333, 334, 345, 347, 369
aldol addition · 392
Aldol Condensation · 393, 394
Alkene Metathesis · 320
alkylidene complex · 325, 326
Allylic · 288, 290
allylic halogenation · 290
Alpha Halogenation · 390
alpha-alkylation · 388
alpha-Cleavage · 433
amidation · 375
ammonolysis · 375
angle strain · 80
Anhydrides · 346
aniline · 250, 297
anisole · 250
Anti- Addition · 165
anti addition of hydrogen to alkyne · 205
antiaromatic · 244
antibonding orbital · 408
anti-Markovnikov · 188
antiperiplanar · 127
Aromaticity · 243, 244, 246
Arrhenius · 47
Arrow-Pushing Formalism · 30
Assigning R- and S- · 89
Assigning R- and S- Labels of Configuration · 91
axial · 82
B
backside attack · 119
Basicity · 104, 246
Beer-Lambert Law · 412
benzaldehyde · 250
benzonitrile · 250
benzoyl peroxide · 290
benzylic · 282, 283, 284, 288, 289, 290, 291
benzylic site · 282, 288, 290
beta-Cleavage · 433
Birch Reduction · 285
Boiling Points · 20, 21
BPO · 290
Bromination · 261
bromoform · 391
Brønsted-Lowry · 47
C
Cahn-Ingold-Prelog Rules · 89
carbaldehyde · 329
carbene · 184, 303
carbenoid · 185, 304
Carbocation Rearrangement · 44, 113
Carbon-13 Nuclear Magnetic Resonance Spectrometry · 423
carboxamide · 347, 417
Chair Conformation of Cyclohexane · 81
Chauvin · 321
chemical shift · 420
chiral center · 86
Chirality · 86
Chlorination · 261
chloroform · 391
Chromium · 282, 333, 334
Cis- · 154
Claisen condensation · 395, 396
Clemmensen Reduction · 283, 357
Competition between Substitution and Elimination Reactions · 132
Configurational Isomerism · 86
Conformational Analysis · 77
Conformational Isomers of Butane · 78, 79
Conformational isomers of Cycloalkanes · 80
Conformational Isomers of Ethane · 77
conjugate addition · 232, 404
Conjugated Dienes · 232
Conjugation · 229
constitutional isomers · 71
Coordination · 44
Coulombic forces · 12
Criteria for Aromaticity · 244
Cross Metathesis · 322
cumulated · 230
Curved Arrows · 30
cycloaddition · 236
Cyclopropanation · 184, 303
D
Decarboxylation · 397
decoupled mode · 424
degree of unsaturation · 159
Delocalization Energy · 38
dextrorotatory · 87
Diastereomers · 96
Diazonium Salts · 297
diazotization reaction · 297
DIBAL-H · 379
Dieckmann Condensation · 395
Diels-Alder Reaction · 236
dimethylsulfoxide · 108
dipole moment · 16
Dipole–Dipole interactions · 19
direct addition · 232, 401, 403, 404
DMF · 108
DMSO · 108
E
E-/Z- Prefix Convention · 156
E1 Mechanism · 121
E2 · 44, 124
eclipsed · 78
Electromagnetic Spectrum · 407
electronic effects · 280, 345, 346
Electrophile · 24
Electrophilic Addition · 44, 162
electrophilic aromatic substitution · 252, 254, 268, 271, 272, 274, 345
Electrophilic Elimination · 44
Elementary Steps of Organic Reactions · 42
Enamines · 356
Enantiomers · 96
Enol · 207
enol form · 335
Enolates · 386, 388, 404
entgegen · 156
envelope distortion · 81
epoxides · 309
Epoxides · 149
equatorial · 82
Equilibria · 62
ester hydrolysis · 369, 375, 397, 398
Ethenolysis · 322
Ether · 145
Examples from the Literature · 23, 29, 57, 85, 93, 98, 110, 142, 148, 179, 214, 224, 228
Exhaustive Hydrogenation · 204
F
fingerprint region · 416
Fischer Esterification · 369, 371, 372
Fischer Projections · 94
fishhook arrow · 30
Formal Charge · 17
Fragmentation · 431
Friedel-Crafts Acylation · 255, 263
Friedel-Crafts Alkylation · 252, 253, 263, 279
fuming sulfuric acid · 258
functional group region · 416
Functional Groups · 25
G
Gabriel Malonic Ester Synthesis of Amino Acids · 400
Gabriel synthesis · 377
Gauche interaction · 78, 83
Gilman Reagents · 300, 308, 312
good nucleophiles · 105
Grignard · 300, 306, 307, 308, 309, 313, 314, 316, 345, 347, 380, 381, 403, 404
Grignard Reagents · 300, 306, 307
Grubbs · 321
H
haloform · 391
Haloform Reaction · 391
Halogenation · 175, 261, 288, 289
Halogenation of Alkanes · 221
Halogenation of alkyne · 198, 200
Halohydrin Formation · 175, 177
Halonium Intermediate · 175
heats of hydrogenation · 229
Heats of Hydrogenation · 60
Heck Reaction · 313
Heterolysis · 44
highest occupied molecular orbital · 407
HOMO · 407
Hückel’s rule · 244
Hybridization · 34
Hybridization on Electronegativity · 37
Hydration · 172, 351
hydration of alkyne · 210
Hydroboration/Oxidation · 188, 211, 337
Hydrogen Bonding · 19
hydrogen deficiency index · 159
Hydrogenation · 60, 159, 160, 204
Hydrohalogenation · 172
Hydrohalogenation of alkyne · 198
hydrolysis · 352, 372, 373, 375, 382
Hydrolysis of Nitriles · 382
hyperconjugation · 58, 63, 184, 267, 271, 272, 273, 303
I
Imines · 355
Inductive Donor · 271
Inductive Effects · 53
Inductive Withdrawing · 267, 274
Infrared Spectroscopy · 415
integral · 426
integration · 426
Intermolecular Forces · 19
iodenium · 261
Iodination · 261
iodoform · 391
IR Band · 417
isolated alkene · 229
Isotopic Abundance · 429
J
Jones Oxidation · 143, 282, 334
K
ketals · 352
keto form · 335, 402
Keto Tautomer · 207
kinetic control · 233, 403
kinetic product · 233, 234
Kumada Reaction · 313
L
Labels of Configuration · 89
LAH · 303
Le Chatelier's principle · 322
leaving group · 111
LeChatelier’s principle · 352, 369, 372
levorotatory · 87
Lewis Definitions · 48
LiAlH4 · 303, 309, 345, 347, 380, 384, 385
ligand exchange reactions · 302
ligands · 301, 302, 308
Limitations of Gilman Reagents · 312
Lindlar’s catalyst · 285
Lindlar's catalyst · 204
line-bond notation · 13
lithium aluminum hydride · 303
London dispersion forces · 19, 20
lowest unoccupied molecular orbital · 407
LUMO · 407
M
magnetically equivalent · 421
Malonic Ester Synthesis · 398, 400
Manganese · 282, 333, 334
manganese dioxide · 282
Mass Spectra of Alkanes · 436
Mass Spectra of Alkenes · 469
Mass Spectra of Alkynes · 477
Mass Spectra of Arenes · 459
Mass Spectra of Branched Cycloalkenes · 476
Mass Spectra of Carbonyls · 448
Mass Spectra of Cycloalkenes · 473
Mass Spectra of Heteroatom-Containing Alkanes · 441
Mass Spectra of Nitriles · 477
McLafferty rearrangement · 434, 448, 449, 452, 454, 455, 459
mCPBA · 182
melting point · 20
Mercurinium Intermediate · 180
Meso Compounds · 97
mesylate · 139
meta- Directors · 274
Metal Hydrides · 300, 309, 348, 351, 355
Michael addition · 404, 405
molar absorptivity · 409, 410
molar extinction coefficient · 409
Molecular Ion · 428
multiplet · 422
multiplicity · 422
N
N,N-dimethylformamide · 108
NaBH4 · 302, 303, 309, 345, 347, 349, 380
Naming Acid Chlorides · 331
Naming Aldehydes · 329
Naming Carboxylic Acids · 330
Naming Esters · 330
Naming Ketones · 330
N-bromosuccinimide · 289
NBS · 289
Newman Projection · 78
N-halosuccinimide · 289
Nitration · 258
Nitronium · 258
NMR active · 419
NMR Spectrum · 420, 423
Nomenclature of Alcohols · 76, 145
Nomenclature of Alkanes · 70
Nomenclature of Alkyl Halides · 71
Nomenclature of Alkynes · 195
Nomenclature of Carbonyls · 329
Nomenclature of Cycloalkanes · 74
Nomenclature of Monosubstituted Benzene Compounds · 250
Nomenclature of Polysubstituted Benzene Compounds · 264
Non-Zaitsev Products · 129
Nuclear Magnetic Resonance · 419
Nucleophile · 24
Nucleophilic Acyl Substitution · 362, 364, 366, 369
Nucleophilic Addition · 44
Nucleophilic Aromatic Substitution · 294
Nucleophilic Carbon · 301
Nucleophilic Elimination · 44
Nucleophilicity · 104
O
Olefin Metathesis · See Alkene Metathesis
Optical Activity · 86
Organolithium · 300, 306, 307
Organometallics · 300, 309
organopalladium · 312
ortho-/para- Directors · 270, 271, 272
osmium tetroxide · 192
oxaphosphetane · 359
Oxidation · 141, 143, 282, 333, 334, 335, 337
oxidation of alcohols · 143
Oxidative Addition · 301
oxonium · 136, 137, 149
Oxymercuration/Demercuration · 335
Oxymercuration/Reduction · 180
Ozonolysis · 190, 338
P
pathlength · 412
PCC · 143, 282, 333, 334
PCl3 · 366, 367, 371
PDC · 333
pericyclic reaction · 236
Peroxide-Mediated Hydrobromination · 217
phenol · 250
Phosphonium Ylides · 359
phosphorus tribromide (PBr3) · 138
phosphorus trichloride · 366
Pi Bonds · 34
pi to pi star transition · 408
polar aprotic solvent · 108
polar protic solvents · 108
polarimeter · 87
Polarity · 15
poor nucleophiles · 105
potassium permanganate · 282
Preparation of Carbonyls · 209
Proton Nuclear Magnetic Resonance Spectrometry · 425, 428
proximity effect · 233
pyridine · 246, 247
pyridinium chlorochromate · 143
Pyridinium Chlorochromate · 333
Pyridinium Dichromate · 333
pyrrole · 246, 247
R
racemate · 87
racemic mixture · 87
Radical Initiation · 218
Radical Propagation · 218
Radical Termination · 219
radicals · 288, 289, 290
Radicals, Stability of · 58
radio frequency (RF) radiation · 419
Rate law, unimolecular substitution · 112
rate of the E1 reaction · 122
rate of the E2 reaction · 124
rate of the SN1 reaction · 112
rate of the SN2 reaction · 115
RCM · 325
reaction coordinate diagram · 233, 266, 402, 403
Reaction Coordinate Diagrams · 66
Reaction of Nitriles · 382
Reaction Rate · 66
Reduction · 141, 282, 283, 284, 285, 357, 358, 379
Reductive Elimination · 301
Relative Rates of Nucleophilic Attack on Carbonyl Functional Groups · 345
Resonance · 38
Resonance Donor · 266, 270
Resonance Stabilization · 52
Retro Diels–Alder · 434
ring flip · 82
ring strain · 80
ring-closing metathesis · 323
Ring-Closing Metathesis · 323
Ring-Opening Metathesis Polymerization · 324
Ring-Opening of Epoxides · 149
Robinson Annulation · 405
ROMP · 324
S
Saytseff’s Rule · 122
Schrock · 320
Sigma · 34
sigma to sigma star transition · 408
Simmons-Smith reaction · 185, 304
SN1 · 252, 294
SN1 Mechanism · 111
SN2 · 294, 301, 309, 359, 367, 382, 385, 397, 398
SNAc · 328, 362, 366, 369, 372, 375, 379, 380, 391, 395
SNAr · 296
SOCl2 · 366, 367, 371, 385
sodium borohydride · 302, 303
solvent cage · 108
Solvent Effects on Basicity and Nucleophilicity · 108, 109
Sonogashira Reaction · 316
Splitting · 423, 426
Spontaneity · 62
staggered conformation · 78
stereocenter · 86
Stereocenters in Reactions · 100
stereochemistry · 314, 330
stereoelectronic effect · 127
stereogenic center · 86
stereorandom reaction · 118
stereoselective · 237, 336
stereospecific reaction · 119
Steric repulsion
steric hindrance · 60
Sterics · 345
Stille Reaction · 314
Strecker amino acid synthesis. · 382, 486
stretching and bending modes · 413
styrene · 250
Substituent Effects on the Rate of Electrophilic Aromatic Substitution · 266
Substituent Effects on the Regiochemistry of Electrophilic Aromatic Substitution · 269
sulfonate ester · 138
Sulfonation · 258
sulfonic acid · 258, 259
sulfonium · 258, 261
Suzuki Reaction · 317
Swern Oxidation · 335
T
TABLE II.4.1 · 165, 166, 167, 168, 169
tautomerization · 335
Tautomerization · 207
tetrahedral intermediate · 341
TFAA · 335
The SN2 Mechanism · 115
thermodynamic control · 233, 403
thermodynamic product · 233, 234
thionyl chloride · 366
thionyl chloride (SOCl2) · 138
toluene · 250
tosylate · 139
Trans- · 154
transesterification · 372, 374
transmetallation · 302, 308, 315, 317, 319
triflate · 139
trifluoroacetic anhydride · 335
U
Ultraviolet · 407
UV-vis spectroscopy · 411
V
valence shell electron pair repulsion (VSEPR) · 13
van der Waals interactions · 19, 20
Vibrational Transitions · 413
Vicinal Diols · 192, 193
W
Wagener, Kenneth B. · 326
Walden inversion · 119
wedge or hashed lines · 13
Wittig Reaction · 359
Wolff–Kishner Reduction · 283, 357
X
xylene · 265
Y
Ylides · 359
Z
Zaitsev’s Rule · 122, 124
zusammen · 156