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.
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 Fetizon oxidation Fleming-Tamao oxidation Ganem oxidation Hass-Bender oxidation Jones oxidation Kornblum oxidation Krohnke oxidation Lemieux-Johnson oxidation Ley oxidation Malaprade reaction Nucleophilic epoxidation Oppenauer oxidation Parikh-Doering oxidation Pfitzner-Moffatt oxidation Pinnick oxidation Prilezhaev reaction Riley oxidation Rubottom oxidation Saegusa-Ito oxidation Sarett oxidation Schmidt reaction Seyferth-Gilbert homologation Sommelet reaction Stahl oxidation Swern oxidation Tamao oxidation Tollens oxidation Wacker-Tsuji oxidation
Pericyclic Reactions Cheletropic reaction Dyotropic reaction Electrocyclic reaction Group transfer reaction Sigmatropic reaction
Polymerization Reactions Cationic polymerization Anionic polymerization Radical polymerization Ring-opening polymerization
Rearrangement Reactions Allylic rearrangement Amadori rearrangement Aston-Greenburg rearrangement Aza-Cope rearrangement Baeyer-Villiger rearrangement Baker–Venkataraman rearrangement Bamberger rearrangement Beckmann rearrangement Bellus-Claisen rearrangement Benzidine rearrangement Benzilic acid rearrangement Brook rearrangement Carroll rearrangement Chapman rearrangement Ciamician-Dennstedt rearrangement Claisen rearrangement Cope rearrangement Cornforth rearrangement Criegee rearrangement Curtius rearrangement Demjanov rearrangement Dienol-benzene rearrangement Dienone-phenol rearrangement Dimroth rearrangement Di-π-methane rearrangement Favorskii rearrangement Ferrier reaction Fischer-Hepp rearrangement Fries rearrangement Fritsch-Buttenberg-Wiechell rearrangement Gabriel-Colman rearrangement Hayashi rearrangement Hock rearrangement Hofmann rearrangement Hofmann-Martius rearrangement Homo-rearrangement of steroids Ireland–Claisen rearrangement Jacobsen rearrangement Johnson-Claisen rearrangement Kornblum-DeLaMare rearrangement Lossen rearrangement McLafferty rearrangement Meisenheimer rearrangement Metal-ion-catalyzed σ-bond rearrangement Meyer-Schuster rearrangement Mislow-Evans rearrangement Nametkin rearrangement Neber rearrangement Newman–Kwart rearrangement Orton rearrangement Overman rearrangement Oxy-Cope rearrangement Payne rearrangement Perkin rearrangement Piancatelli rearrangement Pinacol rearrangement Pummerer rearrangement Reilly-Hickinbottom rearrangement Retropinacol rearrangement Rupe rearrangement Semidine rearrangement Smiles rearrangement Sommelet-Hauser rearrangement Stevens rearrangement Stieglitz rearrangement Tafel rearrangement Tiemann rearrangement Tiffeneau-Dernjanov rearrangement Truce-Smiles rearrangement Wagner-Meerwein rearrangement Wallach rearrangement Wessely-Moser rearrangement Westphalen-Lettre rearrangement Willgerodt rearrangement Wittig rearrangement 1,2-Wittig rearrangement 2,3-Wittig rearrangement Wolff rearrangement Von Richter reaction
Reduction Reactions Bechamp reduction Birch reduction Bouveault-Blanc reduction Carbonyl reduction CBS reduction Clemmensen reduction Corey-Bakshi-Shibata reduction Corey–Itsuno reduction DIBAL-H selective reduction Evans-Saksena reduction Evans-Tishchenko reaction Eschweiler-Clarke reaction Fukuyama reduction Luche reduction Marko-Lam deoxygenation Meerwein-Ponndorf-Verley reduction Midland Alpine borane reduction Mozingo reduction Narasaka-Prasad reduction Noyori asymmetric hydrogenation Rosenmund reduction Staudinger reduction Stephen aldehyde synthesis Tishchenko reaction Wolff-Kishner reduction Zinin reduction
Substitution Reactions Electrophilic Aliphatic Substitution Reactions Carbene C–H insertion Carbonyl α-substitution reaction Dizaonium coupling Keto-enol tautomerism Ketone halogenation Nitrosation Electrophilic Aromatic Substitution (EAS) Reactions Bischler-Napieralski synthesis Blanc halomethylation Combes synthesis Friedel-Crafts acylation Friedel-Crafts alkylation Fries rearrangement Gatterman reaction Houben-Hoesch reaction Kolbe-Schmitt reaction Lehmstedt-Tanasescu reaction Pechmann condensation Pictet-Spengler reaction Pomeranz-Fritsch reaction Quelet reaction Reimer-Tiemann reaction Tscherniac-Einhorn reaction Vilsmeier-Haack reaction Von Pechmann reaction Nucleophilic Acyl Substitution (SNAcyl) Reactions Fischer esterification Nucleophilic Aromatic Substitution (SNAr) Reactions Balz-Schiemann reaction Bamberger rearrangement Chichibabin reaction Smiles rearrangement Vicarious nucleophilic substitution Nucleophilic Substitution (SN) Reactions Baeyer-Villiger oxidation Delépine reaction Dess-Martin oxidation Ferrier rearrangement Finkelstein reaction Gabriel synthesis Kolbe nitrile synthesis Michaelis-Arbuzov reaction Mitsunobu reaction Perkow reaction Sandmeyer reaction Sharpless asymmetric dihydroxylation Sharpless oxyamination Solvolysis reaction Pinner reaction Swern oxidation Tishchenko reaction Wacker oxidation Wenker synthesis Williamson ether synthesis Radical Substitution Minisci reaction
See also Important publications in organic chemistry List of organic reactions
References
External links
Organic Chemistry Lectures, Videos and Text Virtual Textbook of Organic Chemistry Organic Families and Their Functional Groups Roger Frost's Organic Chemistry - multimedia teaching tools