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cases or are mainly of academic interest disproportionation of an aldehyde in the cannizzaro reaction rearrangement of diketones in the benzilic acid rearrangement involving the generation of benzoic acids are the von richter reaction from nitrobenzenes and the kolbe schmitt reaction from phenols reactions edit carboxylic acid organic reactions acid base reactions edit carboxylic acids react with bases to form carboxylate salts in which the hydrogen of the hydroxyl oh group is replaced with a metal cation for example acetic acid found in vinegar reacts with sodium bicarbonate baking soda to form sodium acetate carbon dioxide and water ch 3 cooh nahco 3 ch 3 coo na co 2 h 2 o conversion to esters amides anhydrides edit widely practiced reactions convert carboxylic acids into esters amides carboxylate salts acid chlorides acid anhydrides and alcohols their conversion to esters is widely used e g in the production of polyesters likewise carboxylic acids are converted into amides but this conversion typically does not occur by direct reaction of the carboxylic acid and the amine instead esters are typical precursors to amides the conversion of amino acids into peptides is a significant biochemical process that requires atp converting a carboxylic acid to an amide is possible but not straightforward instead of acting as a nucleophile an amine will react as a base in the presence of a carboxylic acid to give the ammonium carboxylate salt heating the salt to above 100 c will drive off water and lead to the formation of the amide this method of synthesizing amides is industrially important and has laboratory applications as well 20 in the presence of a strong acid catalyst carboxylic acids can condense to form acid anhydrides the condensation produces water however which can hydrolyze the anhydride back to the starting carboxylic acids thus the formation of the anhydride via condensation is an equilibrium process citation needed under acid catalyzed conditions carboxylic acids will react with alcohols to form esters via the fischer esterification reaction which is also an equilibrium process alternatively diazomethane can be used to convert an acid to an ester while esterification reactions with diazomethane often give quantitative yields diazomethane is only useful for forming methyl esters 20 reduction edit like esters most carboxylic acids can be reduced to alcohols by hydrogenation or using hydride transferring agents such as lithium aluminium hydride strong alkyl transferring agents such as organolithium compounds but not grignard reagents will reduce carboxylic acids to ketones along with transfer of the alkyl group citation needed the vilsmaier reagent n n dimethyl chloromethylene ammonium chloride clhc n ch 3 2 cl is a highly chemoselective agent for carboxylic acid reduction it selectively activates the carboxylic acid to give the carboxymethyleneammonium salt which can be reduced by a mild reductant like lithium tris t butoxy aluminum hydride to afford an aldehyde in a one pot procedure this procedure is known to tolerate reactive carbonyl functionalities such as ketone as well as moderately reactive ester olefin nitrile and halide moieties 21 conversion to acyl halides edit the hydroxyl group on carboxylic acids may be replaced with a chlorine atom using thionyl chloride to give acyl chlorides in nature carboxylic acids are converted to thioesters thionyl chloride can be used to convert carboxylic acids to their corresponding acyl chlorides first carboxylic acid 1 attacks thionyl chloride and chloride ion leaves the resulting oxonium ion 2 is activated towards nucleophilic attack and has a good leaving group setting it apart from a normal carboxylic acid in the next step 2 is attacked by chloride ion to give tetrahedral intermediate 3 a chlorosulfite the tetrahedral intermediate collapses with the loss of sulfur dioxide and chloride ion giving protonated acyl chloride 4 chloride ion can remove the proton on the carbonyl group giving the acyl chloride 5 with a loss of hcl phosphorus iii chloride pcl 3 and phosphorus v chloride pcl 5 will also convert carboxylic acids to acid chlorides by a similar mechanism one equivalent of pcl 3 can react with three equivalents of acid producing one equivalent of h 3 po 3 or phosphorus acid in addition to the desired acid chloride pcl 5 reacts with carboxylic acids in a 1 1 ratio and produces phosphorus v oxychloride pocl 3 and hydrogen chloride hcl as byproducts citation needed reactions with carbanion equivalents edit carboxylic acids react with grignard reagents and organolithiums to form ketones the first equivalent of nucleophile acts as a base and deprotonates the acid a second equivalent will attack the carbonyl group to create a geminal alkoxide dianion which is protonated upon workup to give the hydrate of a ketone because most ketone hydrates are unstable relative to their corresponding ketones the equilibrium between the two is shifted heavily in favor of the ketone for example the equilibrium constant for the formation of acetone hydrate from acetone is only 0 002 the carboxylic group is the most acidic in organic compounds 22 specialized reactions edit as with all carbonyl compounds the protons on the α carbon are labile due to keto enol tautomerization thus the α carbon is easily halogenated in the hell volhard zelinsky halogenation the schmidt reaction converts carboxylic acids to amines carboxylic acids are decarboxylated in the hunsdiecker reaction the dakin west reaction converts an amino acid to the corresponding amino ketone in the barbier wieland degradation a carboxylic acid on an aliphatic chain having a simple methylene bridge at the alpha position can have the chain shortened by one carbon the inverse procedure is the arndt eistert synthesis where an acid is converted into acyl halide which is then reacted with diazomethane to give one additional methylene in the aliphatic chain many acids undergo oxidative decarboxylation enzymes that catalyze these reactions are known as carboxylases ec 6 4 1 and decarboxylases ec 4 1 1 carboxylic acids are reduced to aldehydes via the ester and dibal via the acid chloride in the rosenmund reduction and via the thioester in the fukuyama reduction in ketonic decarboxylation carboxylic acids are converted to ketones organolithium reagents 2 equiv react with carboxylic acids to give a dilithium 1 1 diolate a stable tetrahedral intermediate which decomposes to give a ketone upon acidic workup the kolbe electrolysis is an electrolytic decarboxylative dimerization reaction it gets rid of the carboxyl groups of two acid molecules and joins the remaining fragments together carboxyl radical edit the carboxyl radical cooh only exists briefly 23 the acid dissociation constant of cooh has been measured using electron paramagnetic resonance spectroscopy 24 the carboxyl group tends to dimerise to form oxalic acid citation needed see also edit list of carboxylic acids pseudoacid thiocarboxylic acid references edit iupac compendium of chemical terminology 5th ed the gold book 2025 online version 2006 carboxylic acids doi 10 1351 goldbook c00852 recommendations 1979 organic chemistry iupac nomenclature rules c 4 carboxylic acids and their derivatives 1 2 favre henri a powell warren h 17 december 2013 p 65 nomenclature of organic chemistry the royal society of chemistry doi 10 1039 9781849733069 isbn 978 0 85404 182 4 1 2 morrison r t boyd r n 1992 organic chemistry 6th ed prentice hall isbn 0 13 643669 2 physical properties of carboxylic acids chemistry libretexts retrieved 24 august 2026 carboxylic acid structure properties formula uses facts britannica www britannica com retrieved 26 may 2025 ahluwalia v k 2023 organic reactions and their mechanisms cham springer international publishing pp 11 15 doi 10 1007 978 3 031 15695 3_1 isbn 978 3 031 15694 6 retrieved 15 june 2025 citation missing or empty title help haynes william m ed 2011 crc handbook of chemistry and physics 92nd ed crc press pp 5 94 to 5 98 isbn 978 1439855119 chlorocarbonic acid human metabolome database mcmurry john 2015 organic chemistry 9th ed cengage learning pp 798 802 isbn 978 1 305 08048 5 smith brian november 2018 the c o bond part viii review spectroscopy november 2018 33 24 29 retrieved 12 february 2024 chapter 13 carbonyl compounds ketones aldehydes carboxylic acids pdf university of california riverside retrieved 22 june 2026 nora angelo szczepanek alfred koenen gunther 2001 metallic soaps ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a16_361 isbn 3527306730 sharkey td may 2019 discovery of the canonical calvin benson cycle photosynthesis research 140 2 235 252 bibcode 2019phore 140 235s doi 10 1007 s11120 018 0600 2 osti 1607740 pmid 30374727 s2cid 53092349 riemenschneider wilhelm 2002 carboxylic acids aliphatic ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a05_235 isbn 3527306730 mohammadpoor baltork iraj sadeghi majid m adibi abol hassan 31 october 2001 efficient solvent free oxidation of organic compounds with potassium dichromate in the presence of lewis acids molecules 6 11 900 908 doi 10 3390 61100900 issn 1420 3049 pmc 6236395 henry gilman r h kirby 1925 dl methylethylacetic acid organic syntheses 5 75 doi 10 15227 orgsyn 005 0075 s v puntambeker e a zoellner l t sandborn e w bousquet 1928 trimethylacetic acid organic syntheses 8 104 doi 10 15227 orgsyn 008 0104 cite journal cs1 maint multiple names authors list link perry c reeves 1977 carboxylation of aromatic compounds ferrocenecarboxylic acid org synth 56 28 doi 10 15227 orgsyn 056 0028 1 2 wade 2010 pp 964 965 fujisawa tamotsu sato toshio reduction of carboxylic acids to aldehydes 6 ooxdecanal organic syntheses 66 121 doi 10 15227 orgsyn 066 0121 collected volumes vol 8 p 498 wade 2010 p 838 milligan d e jacox m e 1971 infrared spectrum and structure of intermediates in reaction of oh with co journal of chemical physics 54 3 927 942 bibcode 1971jchph 54 927m doi 10 1063 1 1675022 the value is p k a 0 2 0 1 jeevarajan a s carmichael i fessenden r w 1990 esr measurement of the p k a of carboxyl radical and ab initio calculation of the carbon 13 hyperfine constant journal of physical chemistry 94 4 1372 1376 bibcode 1990jphch 94 1372j doi 10 1021 j100367a033 external links edit look up carboxyl in wiktionary the free dictionary carboxylic acids ph and titration freeware for calculations data analysis simulation and distribution diagram generation phc archived 1 may 2021 at the wayback machine v t e functional groups hydrocarbons only c and h alkyl methyl ethyl propyl cyclopropyl butyl pentyl methylene bridge methine alkene vinyl allyl 1 propenyl crotyl allene cumulene aryl phenyl benzyl alkyne carbene only carbon hydrogen and oxygen only c h and o r o r acetal alcohol alkoxy methoxy ether enol ether epoxide peroxy hydroperoxy dioxiranes ethylenedioxy methylenedioxy carbonyl acyl acetyl acryloyl benzoyl aldehyde ketene ketone ynone reductone carboxy carboxyl acetoxy anhydride ester orthoester only one element not being carbon hydrogen or oxygen one element not c h or o nitrogen amine enamine ammonium hydrazo nitrene imine oxime hydrazone azo amide imidate amidine carbamate imide nitrile isonitrile cyanate isocyanate nitrate nitrite nitro nitroso nonoate triazole tetrazole silicon silane hydrosilane chlorosilane silene silanol siloxide siloxane silanone silether silole silatrane silicate phosphorus phosphate phosphodiester phosphonate phosphite phosphonous phosphinate phosphine oxide phosphine phosphonium phosphaalkene phosphaalkyne phosphaallene arsenic arsinic acid arsonic acid arsole sulfur thiol thioether sulfonium thia crown ether persulfide disulfide sulfenic acid thiosulfinate sulfoxide thiosulfonate sulfinic acid sulfone sulfonic acid thioketone thial thioester thionoester thioxanthate xanthate boron boronic acid borinic acid selenium selenol selenonic acid seleninic acid selenenic acid selone selenoether tellurium tellurol telluroketone telluroether polonium polonol polonoether halo haloalkane fluoroethyl trifluoromethyl trichloromethyl trifluoromethoxy hypervalent iodine vinyl halide iodide acyl halide chloride perchlorate other isothiocyanate phosphoramides sulfenyl chloride sulfonamide thiocyanate sulfinylamines see also chemical classification chemical nomenclature inorganic organic v t e topics in organic reactions addition reaction elimination reaction polymerization reagents rearrangement reaction redox reaction regioselectivity stereoselectivity stereospecificity substitution reaction a value alpha effect annulene anomeric effect antiaromaticity aromatic ring current aromaticity baird s rule baker nathan effect baldwin s rules bema hapothle beta silicon effect bicycloaromaticity bredt s rule bürgi dunitz angle catalytic resonance theory charge remote fragmentation charge transfer complex clar s rule conformational isomerism conjugated system conrotatory and disrotatory curtin hammett principle dynamic binding chemistry edwards equation effective molarity electromeric effect electron rich electron withdrawing group electronic effect electrophile evelyn effect flippin lodge angle free energy relationship grunwald winstein equation hammett acidity function hammett equation george s hammond hammond s postulate homoaromaticity hückel s rule hyperconjugation inductive effect kinetic isotope effect lfer solvent coefficients data page marcus theory markovnikov s rule möbius aromaticity möbius hückel concept more o ferrall jencks plot negative hyperconjugation neighbouring group participation 2 norbornyl cation nucleophile kennedy j p orton passive binding phosphaethynolate polar effect polyfluorene ring strain σ aromaticity spherical aromaticity spiroaromaticity steric effects superaromaticity swain lupton equation taft equation thorpe ingold effect vinylogy walsh diagram woodward hoffmann rules woodward s rules y aromaticity yukawa tsuno equation zaitsev s rule σ bishomoaromaticity list of organic reactions carbon carbon bond forming reactions acetoacetic ester synthesis acyloin condensation aldol condensation aldol reaction alkane metathesis alkyne metathesis alkyne trimerisation alkynylation allan robinson reaction arndt eistert reaction auwers synthesis aza baylis hillman reaction barbier reaction barton kellogg reaction baylis hillman reaction benary reaction bergman cyclization biginelli reaction bingel reaction blaise ketone synthesis blaise reaction blanc chloromethylation bodroux chichibabin aldehyde synthesis bouveault aldehyde synthesis bucherer bergs reaction buchner ring expansion cadiot chodkiewicz coupling carbonyl allylation carbonyl olefin metathesis castro stephens coupling chan rearrangement chan lam coupling claisen condensation claisen rearrangement claisen schmidt condensation combes quinoline synthesis corey fuchs reaction corey house synthesis coupling reaction cross coupling reac...