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Organic Chemistry -Free Course

Index
Click the link to go to the appropriate lesson. You can get a Paper version of the booksAmazon link for Organic 1 Primer or Amazon link for Organic 2 Primer.

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

 

 

 

 

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