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Acetic acid - Chemical properties | | Acetic acid - Chemical properties: Encyclopedia II - Acetic acid - Chemical properties | | The hydrogen (H) atom in the carboxyl group (−COOH) in carboxylic acids such as acetic acid can be given off as an H+ ion (proton), giving them their acidic character. Acetic acid is a weak, effectively monoprotic acid in aqueous solution, with a pKa value of 4.8. A 1.0 M solution (about the concentration of domestic vinegar) has a pH of 2.4, indicating that merely 0.4% of the ...
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| | | Acetic acid: Encyclopedia II - Acetic acid - Chemical properties
Acetic acid - Chemical properties
Acidity
The hydrogen (H) atom in the carboxyl group (−COOH) in carboxylic acids such as acetic acid can be given off as an H+ ion (proton), giving them their acidic character. Acetic acid is a weak, effectively monoprotic acid in aqueous solution, with a pKa value of 4.8. A 1.0 M solution (about the concentration of domestic vinegar) has a pH of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated.
Cyclic dimer
The crystal structure of acetic acid[4] shows that the molecules pair up into dimers connected by hydrogen bonds. The dimers can also be detected in the vapour at 120 °C. They probably also occur in the liquid phase of pure acetic acid, but are rapidly disrupted if any water is present. This dimerisation behaviour is shared by other lower carboxylic acids.
Solvent
Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water. With a moderate dielectric constant of 6.2, it can dissolve not only polar compounds such as inorganic salts and sugars, but also non-polar compounds such as oils and elements such as sulfur and iodine. It readily mixes with many other polar and non-polar solvents such as water, chloroform, and hexane. This dissolving property and miscibility of acetic acid makes it a widely used industrial chemical.
Chemical reactions
Acetic acid is corrosive to many metals including iron, magnesium, and zinc, forming hydrogen gas and metal salts called acetates. Aluminium, when exposed to oxygen, forms a thin layer of aluminium oxide on its surface which is relatively resistant, so that aluminium tanks can be used to transport acetic acid. Metal acetates can also be prepared from acetic acid and an appropriate base, as in the popular "baking soda + vinegar" reaction. With the notable exception of chromium(II) acetate, almost all acetates are soluble in water.
Mg(s) + 2 CH3COOH(aq) → (CH3COO)2Mg(aq) + H2(g)
NaHCO3(s) + CH3COOH(aq) → CH3COONa(aq) + CO2(g) + H2O(l)
Acetic acid undergoes the typical chemical reactions of a carboxylic acid, notably the formation of ethanol by reduction, and formation of derivatives such as acetyl chloride via nucleophilic acyl substitution. Other substitution derivatives include acetic anhydride; this anhydride is produced by loss of water from two molecules of acetic acid. Esters of acetic acid can likewise be formed via Fischer esterification, and amides can also be formed. When heated above 440 °C, acetic acid decomposes to produce carbon dioxide and methane, or to produce ketene and water.
Detection
Acetic acid can be detected by its characteristic smell. A colour reaction for salts of acetic acid is iron(III) chloride solution, which results in a deeply red colour that disappears after acidification. Acetates when heated with arsenic trioxide form cacodyl oxide, which can be detected by its malodorous vapours.
Other related archivesAcetaldehyde, Acetate, Acetic acid (data page), Acetic acid bacteria, Acetic anhydride, Acetobacter, Acetyl group, Acetyl-coenzyme A, Aluminium, Andreas Libavius, BASF, BP Chemicals, British Celanese, C2H4, C2H5OH, C4H10, C6H12O6, CH3CHO, CH3COONa, CH3I, CH3OH, CO, CO2, Carboxylic acid, Cativa, Celanese, Chloroacetic acids, Clostridium, Clostridium acetobutylicum, Copper(II) acetate, Descaling agent, E262, EU classification, Eastman, Esters, Ethanol, Ethyl acetate, European, Fatty acid, Fischer esterification, Formic acid, Friedel-Crafts alkylation, German, Greek, H2, H2O, H3C-CO-O-CH=CH2, H3C-CO-O-R, H+, HI, HO-R, Heck reaction, Hermann Kolbe, IUPAC, Jabir Ibn Hayyan (Geber), Japan, Latex, Latin, Liquid, M, Mg, Millennium Chemicals, Monochloroacetic acid, Monsanto, Monsanto process, NaHCO3, O2, Oita, Palladium(II) acetate, Pickling, Pierre Adet, Propionic acid, Renaissance, Romans, Samsung, Saturn, Showa Denko, Sodium acetate, Sterling Chemicals, Svensk Etanolkemi, Theophrastos, Tishchenko reaction, Trifluoroacetic acid, United States, Vinegar, Vosol, Wacker process, Wagner-Meerwein rearrangement, above, absorbs, acetaldehyde, acetate, acetates, acetic anhydride, acetogenic bacteria, acetyl, acetyl chloride, acetylation, acid, acid-base reactions, acidity, acidity regulator, acrylic lacquers, actinium, adhesives, air, alcohol, alkyl group, aluminium oxide, amides, anaerobic bacteria, anhydride, aniline, anion, antibacterial, apple cider, aq, aqueous, arsenic trioxide, aryl, aspirin, atm, bacteria, baking soda, base, beer, blood, boiling points, box jellyfish, brewing, butane, butanone, butyl acetate, cacodyl oxide, calcium acetate, camphor, carbocations, carbohydrates, carbon dioxide, carbon disulfide, carbon monoxide, carbon tetrachloride, carboxyl group, carboxylic acid, carboxylic acids, catalysed, catalyst, catalysts, cellulose acetate, charcoal, chemical compound, chemical element, chemical equation, chemical nomenclature, chemical reactions, chemical reagent, chlorination, chloroform, chromium, chromium(II) acetate, coatings, cobalt, coenzyme A, colour reaction, complex, condensation, condiment, convection, copper, copper(II) acetate, corrosive, crystalline, culture, descaling agents, dielectric constant, digestive system, dimers, dissociate, distillation, dry distillation, dyes, electrolytic, elements, empirical formula, ester, esters, ethanol, ethyl acetate, ethyl bromoacetate, ethylene, ethylene oxide, excreted, explosive limits, fats, fatty acids, fermentation, food additive code, food industry, foodstuffs, formaldehyde, formic acid, fungal, fungicide, g, glue, grain, grapes, greener, group, heroin, heteropoly acid, hexane, household, humans, hydrogen, hydrogen bonds, hydrophilic, hygroscopic, indigo dye, inks, inorganic, iodine, iodomethane, ion, ions, iridium, iron, iron(II) acetate, iron(III) chloride, isobutyl acetate, ketene, l, lead acetate, lead carbonate, lead poisoning, limescale, liquid, loss of water, magnesium, malodorous, malt, manganese, metabolism, metals, methane, methanol, milk of lime, miscibility, monomer, monoprotic acid, mordants, must, naphtha, nitrile rubber, nitro, nitrocellulose, nucleophile, nucleophilic acyl substitution, organic, organic synthesis, outer ear infections, oxidation, oxygen, pH, pKa, paints, palladium, perchloric acid, peroxides, petrochemical, photographic film, pickling, pigment, pigments, polar, polyethylene terephthalate, polymers, polyvinyl acetate, potato, preservative, pressures, primates, propionic acid, propyl acetate, propylene oxide, protic solvent, proton, pyrolysis, reagent, rearranged, recrystallisation, reducing, reduction, rhodium, rice, ruthenium, s, salt, silage, soil, solid, solutions, solvent, solvents, stop bath, sugars, sulfur, sulfuric acid, synthesised, temperature, terephthalic acid, tetrachloroethylene, textile, tonnes, tons, triacetin, trichloroacetic acid, triglycerides, trivial name, tungstosilicic acid, vaginal lubrication, varnish, verdigris, vinegar, vinyl acetate monomer (VAM), water, weak acid, wine, winemaking, yeast, zinc, °C
 Adapted from the Wikipedia article "Chemical properties", under the G.N U Free Docmentation License. Please also see http://en.wikipedia.org/wiki |
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