Carboxylic acid

Definition

In organic chemistry, a carboxylic acid is a polar, organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Carboxylic acids are often considered weak acids as they only partially ionise (dissociate) in water.

Related concepts

(4+3) cycloaddition 1,2-Wittig rearrangement 1,2-rearrangement 1,3-Dipolar cycloaddition 1-Phosphaallenes 2,3-Wittig rearrangement 2,3-sigmatropic rearrangement 2-Furoic acid 2-Nitrobenzoic acid 2-Norbornyl cation 3-chloropropanoic acid 4+4 Photocycloaddition 6+4 Cycloaddition A value Acetal Acetate Acetic acid Acetoacetic acid Acetoacetic ester synthesis Acetone Acetoxy group Acetyl group Acetylene Achmatowicz reaction Acid anhydride Acid chloride Acid chlorides Acid dissociation constant Acrylic acid Acryloyl group Acyl chloride Acyl group Acyl halide Acyloin condensation Addition reaction Adenosine triphosphate Adipic acid Adkins–Peterson reaction Akabori amino-acid reaction Alcohol (chemistry)Alcohol oxidation Alcohols Aldaric acid Aldehyde Aldol condensation Aldol reaction Algar–Flynn–Oyamada reaction Alkane metathesis Alkene Alkenes Alkenyl Alkoxy group Alkyl Alkyne Alkyne metathesis Alkyne trimerisation Alkyne zipper reaction Alkynes Alkynylation Allan–Robinson reaction Allenes Allen–Millar–Trippett rearrangement Allyl group Allylic rearrangement Alpha-carbon Alpha-ketol rearrangement Alpha effect Alpha hydroxy acid Amadori rearrangement Amide Amide (functional group)Amide reduction Amides Amidine Amine Amino acid Andrussow process Angeli–Rimini reaction Anion Annulation Annulene Anomeric effect Antiaromaticity Arachidic acid Arndt–Eistert reaction Arndt–Eistert synthesis Aromatic compound Aromatic ring current Aromaticity Aromatization Arsenic Arsinic acid Arsole Arsonic acid (functional group)Aryl Aspirin Autoxidation Auwers synthesis Aza-Baylis–Hillman reaction Aza-Cope rearrangement Aza-Diels–Alder reaction Azide-alkyne Huisgen cycloaddition Azo compound Azo coupling Baeyer–Emmerling indole synthesis Baeyer–Villiger oxidation Baird's rule Baker–Nathan effect Baker–Venkataraman rearrangement Baldwin's rules Bamberger rearrangement Bamberger triazine synthesis Bamford–Stevens reaction Banert cascade Barbier reaction Barbier–Wieland degradation Bartoli indole synthesis Barton–Kellogg reaction Barton–McCombie deoxygenation Barton–Zard reaction Base (chemistry)Baylis–Hillman reaction Bechamp reduction Beckmann rearrangement Bema Hapothle Benary reaction Benkeser reaction Benzilic acid rearrangement Benzoic acid Benzoyl group Benzyl group Bergman cyclization Bergmann degradation Bernthsen acridine synthesis Beta-silicon effect Beta hydroxy acid Bicarbonate buffer system Bicycloaromaticity Biginelli reaction Bingel reaction Birch reduction Bischler–Möhlau indole synthesis Bischler–Napieralski reaction Blaise ketone synthesis Blaise reaction Blanc chloromethylation Blum–Ittah aziridine synthesis Bobbitt reaction Bodroux–Chichibabin aldehyde synthesis Body odour Boekelheide reaction Boger pyridine synthesis Bohlmann–Rahtz pyridine synthesis Bohn–Schmidt reaction Boord olefin synthesis Borinic acid Boron Boronic acid Borsche–Drechsel cyclization Bosch reaction Boudouard reaction Bouveault aldehyde synthesis Bouveault–Blanc reduction Boyland–Sims oxidation Bradsher cycloaddition Bredt's rule Brook rearrangement Brønsted–Lowry acid–base theory Bucherer carbazole synthesis Bucherer–Bergs reaction Buchner ring expansion Butter Butyl group Butyric acid Bürgi–Dunitz angle CRC Handbook of Chemistry and Physics CRC Press Cadiot–Chodkiewicz coupling Cadogan–Sundberg indole synthesis Camps quinoline synthesis Cannizzaro reaction Capric acid Caproic acid Caprylic acid Carbamate Carbene Carbocation Carbolic acid Carbon Carbon dioxide Carbon monoxide Carbonation Carbonic acid Carbonyl Carbonyl allylation Carbonyl group Carbonyl olefin metathesis Carbonyl reduction Carboxylase Carboxylate Carboxylic acid reduction Carboxylic anhydride Carroll rearrangement Castro–Stephens coupling Catalytic resonance theory Cation Cativa process Chan rearrangement Chan–Lam coupling Charge-transfer complex Charge remote fragmentation Cheletropic reaction Chemical classification Chemical nomenclature Chichibabin pyridine synthesis Chloroacetic acid Chloroformic acid Chlorosilane Chocolate Chugaev elimination Citric acid Citrus fruit Claisen-Schmidt condensation Claisen condensation Claisen rearrangement Clar's rule Clemmensen reduction Coconut oil Coconuts Collins oxidation Combes quinoline synthesis Condensation reaction Conformational isomerism Conia-ene reaction Conjugate acid Conjugated system Conrotatory and disrotatory Cooh (musician)Cook–Heilbron thiazole synthesis Cope reaction Cope rearrangement Corey–Fuchs reaction Corey–House synthesis Corey–Itsuno reduction Corey–Kim oxidation Corey–Winter olefin synthesis Cornforth rearrangement Coupling reaction Criegee oxidation Criegee rearrangement Cross-coupling partner Cross-coupling reaction Cross dehydrogenative coupling Crotyl group Cumulene Curtin–Hammett principle Curtius rearrangement Cyanate ester Cycloaddition Cyclopropanation Cyclopropyl DNA oxidation Dakin oxidation Dakin–West reaction Darzens reaction Davis oxidation Davis–Beirut reaction De Kimpe aziridine synthesis Debus–Radziszewski imidazole synthesis Decarboxylase Dehydrohalogenation Demjanov rearrangement Deoxygenation Deprotonation Dess–Martin oxidation Di-π-methane rearrangement Diazoalkane 1,3-dipolar cycloaddition Diazomethane Diazonium compound Dicarboxylic acid Dichloroacetic acid Dieckmann condensation Diels–Alder reaction Difluoroacetic acid Diisobutylaluminium hydride Dimer (chemistry)Dimroth rearrangement Dioxirane Dissociation (chemistry)Disulfide Divinylcyclopropane-cycloheptadiene rearrangement Divinylether fatty acids Docosahexaenoic acid Doebner reaction Dowd–Beckwith ring-expansion reaction Dynamic binding (chemistry)Edman degradation Edwards equation Effective molarity Eicosapentaenoic acid Einhorn–Brunner reaction Elbs persulfate oxidation Electrocyclic reaction Electromeric effect Electron-rich Electron-withdrawing group Electron paramagnetic resonance Electronic effect Electrophile Elimination reaction Emde degradation Enamine Enanthic acid Ene reaction Enol ether Enone–alkene cycloadditions Enthalpy of vaporization Enyne metathesis Enzyme Enzyme Commission number Epoxidation of allylic alcohols Epoxide Erlenmeyer–Plöchl azlactone and amino-acid synthesis Eschweiler–Clarke reaction Ester Esterification Esters Ethenolysis Ether Ethyl group Ethylenediaminetetraacetic acid Ethylenedioxy Evelyn effect Fatty acid Favorskii reaction Favorskii rearrangement Feist–Benary synthesis Fermentation (biochemistry)Ferrario–Ackermann reaction Ferrier carbocyclization Ferrier rearrangement Fiesselmann thiophene synthesis Fischer esterification Fischer indole synthesis Fischer oxazole synthesis Fischer–Hepp rearrangement Fischer–Tropsch process Fleming–Tamao oxidation Flippin–Lodge angle Fluoroacetic acid Fluoroethyl Formic acid Free-energy relationship Free radical Friedel–Crafts reaction Friedländer synthesis Fries rearrangement Fritsch–Buttenberg–Wiechell rearrangement Fujimoto–Belleau reaction Fujiwara–Moritani reaction Fukuyama coupling Fukuyama reduction Functional group Gabriel–Colman rearrangement Gallagher–Hollander degradation Ganem oxidation Gattermann reaction Geminal George S. Hammond Gewald reaction Glaser coupling Glyceric acid Glycine Glycol cleavage Glycolic acid Goat Graham reaction Grieco elimination Griesbaum coozonolysis Grignard reaction Grignard reagent Grignard reagents Group transfer reaction Grundmann aldehyde synthesis Grunwald–Winstein equation Haloalkane Halocarbon Haloform reaction Halogen dance rearrangement Halogenation Hammett acidity function Hammett equation Hammick reaction Hammond's postulate Hantzsch ester Hantzsch pyridine synthesis Hayashi rearrangement Heck reaction Hegedus indole synthesis Hell–Volhard–Zelinsky halogenation Hemetsberger indole synthesis Henry reaction Herz reaction Heterogeneous metal catalyzed cross-coupling Hexadehydro Diels–Alder reaction High dilution principle Hiyama coupling Hofmann elimination Hofmann rearrangement Hofmann–Löffler reaction Hofmann–Martius rearrangement Homoaromaticity Homologation reaction Homologation reactions Hooker reaction Horner–Wadsworth–Emmons reaction Hunsdiecker reaction Hurd–Mori 1,2,3-thiadiazole synthesis Hydrazines Hydrazone Hydrazone iodination Hydrocarbon Hydrocarboxylation Hydrocyanation Hydroformylation Hydrogen Hydrogen bond Hydrogen chloride Hydrogenation Hydrogenolysis Hydronium Hydroperoxide Hydrosilane Hydrovinylation Hydroxyl Hydroxylation Hydroxymethylation Hyperconjugation Hückel's rule IUPAC IUPAC books IUPAC nomenclature of inorganic chemistry IUPAC nomenclature of organic chemistry Imidate Imide Imine Inductive effect Infrared spectroscopy Insect stings International Union of Pure and Applied Chemistry Intramolecular Diels–Alder cycloaddition Inverse electron-demand Diels–Alder reaction Iodane Iodolactonization Ireland–Claisen rearrangement Isay reaction Isobutylene Isocitric acid Isocyanate Isocyanide Isosaccharinic acid Isothiocyanate Ivanov reaction Jacobsen epoxidation Jacobsen rearrangement Johnson–Corey–Chaykovsky reaction Jones oxidation Jones reagent Julia olefination Julia–Kocienski olefination Kauffmann olefination Kennedy J. P. Orton Ketene Ketene cycloaddition Keto acid Ketone Ketonic decarboxylation Keto–enol tautomerism Kharasch–Sosnovsky reaction Kiliani–Fischer synthesis Kinetic isotope effect Knoevenagel condensation Knorr pyrrole synthesis Knorr quinoline synthesis Koch reaction Kolbe electrolysis Kolbe–Schmitt reaction Kornblum oxidation Kornblum–DeLaMare rearrangement Kowalski ester homologation Kröhnke pyridine synthesis Kulinkovich reaction Kumada coupling LFER solvent coefficients (data page)Lactic acid Larock indole synthesis Lauric acid Lectka enantioselective beta-lactam synthesis Lehmstedt–Tanasescu reaction Leimgruber–Batcho indole synthesis Leuckart reaction Ley oxidation Liebeskind–Srogl coupling Lindgren oxidation Lipid peroxidation List of carboxylic acids List of organic reactions Lithium aluminium hydride Lithium chloride Lobry de Bruyn–Van Ekenstein transformation Lombardo methylenation Lossen rearrangement Luche reduction Madelung synthesis Maleic acid Malonic ester synthesis Mannich reaction Marcus theory Margaric acid Marker degradation Markovnikov's rule Markó–Lam deoxygenation McCormack reaction McFadyen–Stevens reaction McLafferty rearrangement McMurry reaction Meerwein arylation Meerwein–Ponndorf–Verley reduction Metal-centered cycloaddition reactions Metalloles Methine group Methionine sulfoxide Methoxy group Methoxymethylenetriphenylphosphorane Methyl group Methyl ketone Methylenation Methylene bridge Methylene group Methylenedioxy Meyer–Schuster rearrangement Michael reaction Minisci reaction Mislow–Evans rearrangement Miyaura borylation Mizoroki-Heck vs. Reductive Heck Moiety (chemistry)Molarity More O'Ferrall–Jencks plot Mozingo reduction Mukaiyama hydration Mumm rearrangement Myers allene synthesis Myristic acid Möbius aromaticity Möbius–Hückel concept NONOate Nazarov cyclization reaction Neber rearrangement Nef isocyanide reaction Nef synthesis Negative hyperconjugation Negishi coupling Neighbouring group participation Nenitzescu indole synthesis Newman–Kwart rearrangement Niementowski quinazoline synthesis Niementowski quinoline synthesis Nierenstein reaction Nitrate ester Nitrene Nitrile Nitrite ester Nitro-Mannich reaction Nitro compound Nitrogen Nitrone-olefin (3+2) cycloaddition Nitroso Nonadecylic acid Noyori asymmetric hydrogenation Nozaki–Hiyama–Kishi reaction Nuclear magnetic resonance Nucleophile Nutmeg Nylon Olefin Olefin conversion technology Olefin metathesis Omega hydroxy acid Omega oxidation Oppenauer oxidation Organic Syntheses Organic acid Organic chemistry Organic peroxides Organic reaction Organic redox reaction Organic thiocyanates Organolithium Organolithium reagent Organophosphate Organophosphine Organopolonium chemistry Organosilicon chemistry Organyl group Orthoester Overman rearrangement Oxalic acid Oxidation of primary alcohols to carboxylic acids Oxidative decarboxylation Oxidizing agent Oxime Oxo-Diels–Alder reaction Oxonium ion Oxy-Cope rearrangement Oxygen Oxygen rebound mechanism Oxymercuration reaction Ozonolysis Paal–Knorr synthesis Palladium–NHC complex Palm kernel oil Palm oil Palmitic acid Parent chain Parikh–Doering oxidation Passerini reaction Passive binding Paternò–Büchi reaction Pauson–Khand reaction Peanut oil Pechmann condensation Pelargonic acid Pelargonium Pellizzari reaction Pentadecylic acid Pentyl group Peptide Perchlorate ester Perfume Pericyclic reaction Persulfide Peterson olefination Petrenko-Kritschenko piperidone synthesis Pfitzinger reaction Phenol Phenyl alkanoic acids Phenyl group Pheromone Phosphaalkene Phosphaalkyne Phosphaethynolate Phosphinate Phosphine oxide Phosphite ester Phosphodiester Phosphonate Phosphonite Phosphonium Phosphoramides Phosphorus Phosphorus(III) chloride Phosphorus(V) chloride Phosphorus(V) oxychloride Phosphorus acid Photosynthesis Phthalic acid Piancatelli rearrangement Pictet–Spengler reaction Pinacol coupling reaction Pinacol rearrangement Pinnick oxidation Pivalic acid Polar effect Polarity (chemistry)Polonium Polonium hydride Polyester Polyfluorene Polymerization Pomeranz–Fritsch reaction Potassium dichromate Potassium permanganate Povarov reaction Prato reaction Prilezhaev reaction Prins reaction Propene Propenyl Propionic acid Propyl group Protein Prévost reaction Pschorr cyclization Pseudoacid Pummerer rearrangement Pyruvic acid Quaternary ammonium cation Quelet reaction Ramberg–Bäcklund reaction Rauhut–Currier reaction Rearrangement reaction Reduction of nitro compounds Reductive amination Reductone Reed reaction Reformatsky reaction Regioselectivity Reimer–Tiemann reaction Reissert indole synthesis Resonance stabilized Retro-Diels–Alder reaction Ribulose-1,5-bisphosphate carboxylase/oxygenase Rieche formylation Riley oxidation Ring-closing metathesis Ring expansion and contraction Ring forming reaction Ring strain Robinson annulation Robinson–Gabriel synthesis Rosenmund reduction Rubottom oxidation Ruff degradation Rupe reaction Sabatier reaction Sakurai reaction Salicylic acid Sarett oxidation Schmidt reaction Schotten–Baumann reaction Selenenic acid Selenide Seleninic acid Selenium Selenol Selenonic acid Selenoxide elimination Selone Semipinacol rearrangement Seyferth–Gilbert homologation Shapiro reaction Sharpless asymmetric dihydroxylation Sharpless epoxidation Sharpless oxyamination Sigmatropic reaction Silane Silanol Silanone Silatrane Silicate Silicon Siloxane Siloxide Silyl ether Simmons–Smith reaction Skattebøl rearrangement Skraup reaction Smiles rearrangement Soap making Sodium acetate Sodium bicarbonate Sodium chlorite Sommelet–Hauser rearrangement Sonogashira coupling Spherical aromaticity Spiroaromaticity Stahl oxidation Staudinger reaction Staudinger synthesis Stearic acid Stephen aldehyde synthesis Stereoselectivity Stereospecificity Steric effects Stetter reaction Stevens rearrangement Stieglitz rearrangement Stille reaction Stollé synthesis Stork enamine alkylation Strecker degradation Substituent Substitution reaction Sulfenic acid Sulfenyl chloride Sulfinic acid Sulfinylamine Sulfonamide Sulfone Sulfonic acid Sulfonium Sulfoxide Sulfur Sulfur dioxide Superaromaticity Suzuki reaction Swain–Lupton equation Swern oxidation Taft equation Takai olefination Tartaric acid Telluride (chemistry)Tellurium Telluroketone Tellurol Terephthalic acid Tetrahedral intermediate Tetrazole Thermal rearrangement of aromatic hydrocarbons Thia-crown ether Thial Thiocarboxy Thioester Thioether Thioketone Thiol Thionoester Thionyl chloride Thiosulfinate Thiosulfonate Thioxanthate Thomas D. Sharkey Thorpe reaction Thorpe–Ingold effect Tiffeneau–Demjanov rearrangement Toluene Transfer hydrogenation Triazole Tricarboxylic acid Trichloroacetic acid Trichloromethyl group Tridecylic acid Trifluoroacetic acid Trifluoromethoxy group Trifluoromethyl Trifluoromethyl group Triglyceride Trimethylenemethane cycloaddition Trivial name Ugi reaction Ullmann's Encyclopedia of Industrial Chemistry Ullmann condensation Ullmann reaction Undecylic acid Urech hydantoin synthesis Valerian (herb)Valeric acid Van Leusen reaction Vilsmaier reagent Vinegar Vinyl group Vinyl halide Vinyl iodide functional group Vinylcyclopropane (5+2) cycloaddition Vinylcyclopropane rearrangement Vinylogy Von Braun amide degradation Von Richter reaction Wacker process Wagner-Jauregg reaction Wagner–Meerwein rearrangement Wallach rearrangement Walsh diagram Walter Reppe Water (molecule)Weak acid Weerman degradation Weinreb ketone synthesis Wenker synthesis Westphalen–Lettré rearrangement Wharton reaction Whiting reaction Willgerodt rearrangement Williamson ether synthesis Wittig reaction Wohl degradation Wohl–Aue reaction Wolff rearrangement Wolffenstein–Böters reaction Wolff–Kishner reduction Woodward's rules Woodward–Hoffmann rules Wulff–Dötz reaction Wurtz reaction Wurtz–Fittig reaction Xanthate Xylene Y-aromaticity Yamaguchi esterification Ynone Yukawa–Tsuno equation Zaitsev's rule Zincke–Suhl reaction Zinin reaction Étard reaction Σ-aromaticity Σ-bishomoaromaticity

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