Outline of organic chemistry

The following outline is provided as an overview of and topical guide to organic chemistry:

Organic chemistry is the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of carbon-based compounds, hydrocarbons, and their derivatives. These compounds may contain any number of other elements, including hydrogen, nitrogen, oxygen, the halogens as well as phosphorus, silicon, and sulfur.Robert T. Morrison, Robert N. Boyd, and Robert K. Boyd, Organic Chemistry, 6th edition (Benjamin Cummings, 1992, ) - this is "Morrison and Boyd", a classic textbookJohn D. Roberts, Marjorie C. Caserio, Basic Principles of Organic Chemistry,(W. A. Benjamin, Inc. ,1964) - another classic textbookRichard F. and Sally J. Daley, Organic Chemistry, Online organic chemistry textbook. Ochem4free.info

General topics

History of organic chemistry IUPAC nomenclature of organic chemistry Organic reaction Organic compound Organic synthesis Retrosynthetic analysis

Current trends Current trends in organic chemistry include (as of 2020):

Biocatalysis Biomimetics Catalysis Chemosensors Chiral synthesis Flow chemistry Green chemistry Mechanochemistry Photoredox catalysis

Concepts

Acids and bases Brønsted–Lowry acid–base theory Acid dissociation constants Lewis acids and bases Chemoselectivity Molecular structure Aromaticity Chemical bonding Covalent bonding Lewis model Molecule shapes Bond angles Resonance structures Conjugated systems Functional groups Stereochemistry Conformational isomerism Diastereomer Stereoisomerism Chirality Optical activity Enantiomers Regioselectivity Stereoselectivity Spectroscopy Infrared spectroscopy Mass spectrometry NMR spectroscopy Ultraviolet–visible spectroscopy Supramolecular chemistry Dynamic covalent chemistry Host–guest chemistry Mechanically-interlocked molecular architectures Molecular folding Molecular self-assembly Organometallic chemistry

Chemical species

Acetals Hemiacetals Thioacetals Ketals Acid Anhydrides Acyl Halides Acyl Chlorides Alcohols Diols Geminal Diols Vicinal Diols Fatty Alcohols Silanols Thiols Triols Aldehydes Aldols Alkanes Alkoxides Cycloalkanes Haloalkanes Nitroalkanes Alkenes Vinylidenes Alkynes Enediynes Amides Amidines Lactams Sulfinamides Sulfonamides Sultams Amines Aminals Amino Acids Fatty Amines Hemiaminals Nitrosamines Polyamines Sulfinylamines Azides Brønsted Acids Superacids Carbamates Thiocarbamates Dithiocarbamates Carbohydrates Monosaccharides Disaccharides Oligosaccharides Polysaccharides Carbonates Carbonate Esters Dicarbonates Polycarbonates Thiocarbonates Tricarbonates Carboxylic Acids Carboxylates Cyanates Thiocyanates Isothiocyanates Dicarbonyls Disulfides Enals Enamines Enols Enolates Esters Lactones Sulfonates Thioesters Thiolactones Ethers Epoxides Silyl Ethers Thioethers Glycosides Glycosylamines Heterocyclic Arenes (Aromatics) Benzofurans Benzothiophenes Carbazoles Furans Imidazoles Indoles Indolizines Isoquinolines Olympicenes Oxazoles Purines Xanthines Pyrans Pyrazoles Pyrazines Pyridazines Pyridines Pyrimidines Pyrroles Quinolines Thiazoles Thiophenes Thiopyrans Xanthenes Thioxanthenes Xanthones Heterocyclic Compounds (Non-Aromatic) Aziridines Azetidines Benzoquinones Diazirines Diaziridines Dioxanes Morpholines Oxanes Oxetanes Oxiranes Oxolanes Piperidines Pyrrolidines Quinones Thianes Thietanes Thiiranes Thiolanes Imines Oximes Amidoximes Aldoximes Ketoximes Schiff Bases Imides Ketones Enones Ketenes Lipids Eicosanoids Eoxins Isoprostanes Leukotrienes Lipoxins Prostacyclins Prostanoids Resolvins Thromboxanes Fatty Acids Saturated Fatty Acids Unsaturated Fatty Acids Monounsaturated Fatty Acids Polyunsaturated Fatty Acids Glycolipids Glycoglycerolipids Glycosphingolipids Cerebrosides Sulfatides Gangliosides Globosides Glycophosphatidylinositols Isoprenoids Phospholipids Sphingolipids Ceramides Sphingomyelins Terpenes Monoterpenes Diterpenes Triterpenes Tetraterpenes Sesquiterpenes Sesterterpenes Sesquarterpenes Triglycerides

Macrocyclic Compounds Calixarenes Corroles Crown Ethers Cyclodextrins Fullerenes Porphyrins Mechanically-Interlocked Molecular Architectures Catenanes Olympiadanes Rotaxanes Monocyclic Arenes (Aromatics) Acetophenones Anilines Anisoles Aryl halides Benzene Benzaldehydes Benzamides Benzenesulfonic Acids Benzoic acids Benzophenones Benzyl amines Biphenyls Catechols Chalcones Nitrobenzenes Phenols Thiophenols Toluene Tosylates Brosylates Nosylates Xylenes Nitriles Nucleosides Nucleotides Oligonucleotides Organometallic Compounds Organoboranes Organocuprates Organolithiums Organosilanes Organophosphate Compounds Polyphosphates Phosphazenes Iminophosphoranes Polyphosphazenes Phosphinates Phosphines Diphosphines Phosphinites Phosphites Phosphoramidites Phosphonates Phosphonites Phosphoramidates Phosphoramides Phosphoranes Thiophosphates Phosphorothioate Nucleic Acids Peptides Dipeptides Tripeptides Tetrapeptides Pentapeptides Polypeptides Peroxides Alkenyl Peroxides Peroxyacyl Nitrates Peroxy Acids Polycyclic Arenes (Aromatics) Anthracenes Chrysenes Coronenes Graphenes Naphthalenes Perylenes Phenanthrenes Pyrenes Tetracenes Triphenylenes Polycyclic Compounds (Non-Aromatic) Cubanes Propellanes Polymers Copolymers Graft Polymers Polyphenolic Compounds Flavonoids Anthocyanidins Anthoxanthins Flavones Flavonols Flavanones Flavanonols Flavans Isoflavonoids Lignans Phenolic Acids Stillbenes Tannins Steroids Androstanes Cholanes Cholestanes Estranes Pregnanes Sterols Sulfoxides Surfactants Transition Metal Complexes Transition Metal Aldehyde Complexes Transition Metal Alkene Complexes Transition Metal Arene Complexes Transition Metal Azide Complexes Transition Metal Carbene Complexes Transition Metal Carboxylate Complexes Transition Metal Carbyne Complexes Transition Metal Dithiocarbamates Complexes Transition Metal Ketone Complexes Transition Metal Pyridine Complexes Transition Metal Thiocyanate Complexes Transition Metal Thiolate Complexes Transition Metal Vinylidene Complexes Xanthates Ylides

Reactions

Addition Reactions Electrophilic Addition Reactions Halogen addition reactions Hydration reactions Kucherov reaction Mukaiyama hydration Hydroboration-oxidation reactions Brown hydroboration reaction Hydrohalogenations Noyori asymmetric hydrogenation Oxymercuration reactions Ritter reaction Schwartz hydrozirconation Simmons-Smith reaction Nucleophilic Addition Reactions Aldol Addition Mukaiyama reaction Barbier reaction Baylis-Hillman reaction Blaise reaction Corey-Chaykovsky reaction Cyanohydrin reaction Grignard reaction Horner-Wadsworth-Emmons reaction Mannich reaction Michael 1,2-addition Peterson olefination Pinner reaction Reformatsky reaction Thorpe reaction Wittig reaction Nucleophilic Conjugate Addition Reactions Michael 1,4-addition Stetter reaction Stork enamine alkylation

Annulation Reactions

Danheiser annulation Robinson annulation

Chemical Tests

Barfoed's test Bayer test Benedict's test Biuret test Fehling's test Molisch's test Ninhydrin test Schiff test Seliwanoff's test Tollen's test

Condensation Reactions

Acyloin condensation Aldol condensation Benzoin condensation Claisen condensation Claisen-Schmidt condensation Darzens condensation Dieckmann condensation Fischer-Speier esterification Guareschi-Thorpe condensation Japp-Maitland condensation Knoevenagel condensation Pechmann condensation Rap-Stoermer condensation Stetter reaction Stobbe condensation Ullmann condensation Weiss-Cook condensation Yamaguchi esterification Ziegler condensation

Coupling Reactions

Azo coupling Buchwald-Hartwig coupling Cadiot-Chodkiewicz coupling Castro-Stephens coupling Chan-Lam coupling Eglinton coupling Fukuyama coupling Glaser coupling Hay coupling Heck reaction Hiyama coupling Hirao coupling Kumada coupling Larock indole synthesis Liebeskind-Srogl coupling McMurry reaction Miyaura borylation Negishi coupling Phosphonium coupling Pinacol coupling Prins reaction Pschorr reaction Scholl reaction Sonogashira coupling Stille coupling Suzuki coupling Ugi coupling Ullmann coupling Wurtz coupling

Cyclization Reactions

Bergman cyclization Borsche-Drechsel cyclization Bradsher cyclization Fukuyama indole synthesis Nazarov cyclization Robinson-Gabriel synthesis Simonis chromone cyclization Volhard-Erdmann cyclization

Cycloaddition Reactions

1,3-Dipolar cycloaddition Azide-alkyne Huisgen cycloaddition Diels–Alder reaction Nitrone-olefin (3+2) cycloaddition Staudinger ketene-imine cycloaddition

Degradation Reactions

Barbier-Wieland degradation Bergmann degradation Curtius degradation Darapsky degradation Edman degradation Emde degradation Gallagher-Hollander degradation Grignard degradation Hofmann degradation Ruff-Fenton degradation Schmidt degradation Strecker degradation Von Braun amide degradation Weerman degradation Wohl degradation

Disproportionation Reactions

Cannizzaro Reaction

Elimination Reactions

Beta elimination Chugaev elimination Cope elimination E1cB elimination reaction Hofmann elimination Solvolysis reaction

Epoxidation Reactions

Jacobsen-Katsuki epoxidation Prilezhaev reaction Sharpless epoxidation Shi asymmetric epoxidation

Fragmentation Reactions

Beckmann fragmentation Eschenmoser fragmentation Grob fragmentation

Free Radical Reactions

Barton decarboxylation Barton-McCombie deoxygenation Barton nitrile ester reaction Hofmann-Loffler reaction Hunsdiecker reaction Keck radical allylation Meerwein arylation Minisci reaction Sandmeyer reaction Wohl-Ziegler bromination

Halogenation Reactions

Electrophilic halogenation Halogen addition reaction Free radical halogenation Hell-Volhard-Zelinsky reaction Hunsdiecker reaction Ketone halogenation Kochi reaction

Heterocycle Formation Reactions

Bartoli indole synthesis Biginelli reaction Bischler-Napieralski reaction Bischler-Mohlau indole synthesis Cadogan-Sundberg indole synthesis Ciamician-Dennstedt rearrangement Combes quinolone synthesis Dimroth rearrangement Feist-Benary furan synthesis Fischer indole synthesis Fukuyama indole synthesis Gassman indole synthesis Gutknecht pyrazine synthesis Hantzsch dihydropyridine synthesis Hantzsch pyrrole synthesis Hegedus indole synthesis Heine reaction Hemetsberger indole synthesis Hetero Diels-Alder reaction Hinsburg oxindole synthesis Hofmann-Loffler-Freytag reaction Knorr pyrrole synthesis Knorr pyrazole synthesis Krohnke pyridine synthesis Larock indole synthesis Leimgruber-Batcho indole synthesis Madelung indole synthesis Nenitzescu indole synthesis Paal-Knorr pyrrole synthesis Paterno-Buchi reaction Pechmann pyrazole synthesis Petrenko-Kritschenko piperidone synthesis Pictet-Spengler reaction Piloty-Robinson pyrrole synthesis Pomeranz-Fritsch reaction Reissert indole synthesis Skraup reaction Staedel-Rugheimer pyrazine synthesis Von Pechmann reaction

Homologation Reactions

Arndt-Eistert reaction Corey-Fuchs reaction

Metathesis Reactions

Cross metathesis Enyne metathesis Olefin metathesis Ring closing metathesis Ring opening metathesis

Organometallic Reactions

Synthesis of Organometallic Reagents Grignard reagents Gilman reagents Reformatsky reagents Associative substitution β-hydride elimination Carbometalation Carbon-hydrogen bond activation Cyclometalation Dissociative substitution Electron transfer Hydrometalation Migratory insertion Nucleophilic abstraction Oxidative addition Reductive elimination Transmetalation

Oxidation Reactions

Alcohol oxidation Andrussov oxidation Baeyer-Villiger oxidation Boyland-Sims oxidation Corey-Gilman-Ganem oxidation Corey-Kim oxidation Dakin oxidation Davis oxidation Dess-Martin oxidation Elbs oxidation