Structure of a carboxylic acid

Carboxylic acids, also known as alkanoic acids, are organic acids characterized by the presence of a carboxyl group and have the general chemical formula R-C(=O)-OH, also written as R-COOH, where R is a hydrogen or an alkyl group. The salts and anions of carboxylic acids are called carboxylates. Structure of carboxylic acid, created with ChemSketch This image is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship. ... An organic acid is an organic compound that is an acid. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number Hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1 (IA), 1 , s Density, Hardness 0. ... An alkyl is a functional group of an organic chemical that contains only carbon and hydrogen atoms, which are arranged in a chain. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... For other meanings of the word salt see table salt or salt (disambiguation). ... ...

Acidity, electron distribution and resonance

Carboxylic acids are typically weak acids that partially dissociate into H⁺ cations and RCOO^- anions in aqueous solution. The carboxylate anion R-COO^- is usually named with the suffix "-ate", so acetic acid, for example, becomes acetate ion. Only about 0.02% of all acetic acid molecules are dissociated at room temperature in solution. Dissociation in chemistry and biochemistry is a general process in which complexes, molecules, or salts separate or split into smaller molecules, ions, or radicals, usually in a reversible manner. ... ... ... This article describes water from a scientific and technical perspective. ... The chemical compound acetic acid (from the Latin word acetum, meaning vinegar), systematically called ethanoic acid, is the acid that gives vinegar its sour taste. ...

The two electronegative oxygen atoms tend to pull the electron away from the hydrogen of the hydroxyl group, and the remaining proton H⁺ can more easily leave. The remaining negative charge is then distributed symmetrically among the two oxygen atoms, and the two carbon–oxygen bonds take on a partial double bond character (i.e., they are delocalised). Electronegativity is a measure of the attraction that an atom has for the bonding pair of electrons in a covalent bond. ... Hydroxide is a functional group consisting of oxygen and hydrogen: -O−H It has a charge of 1-. The term hydroxyl group is used when the functional group -OH is counted as a substituent of an organic compound. ... For alternative meanings see proton (disambiguation). ... In chemistry, a chemical bond is the force which holds together atoms in molecules or crystals. ...

This is a result of the resonance structure created by the carbonyl component of the carboxylic acid, without which the OH group does not as easily lose its H⁺ (see alcohol). In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ...

The presence of electronegative groups (such as -OH or -Cl) next to the carboxylic group increases the acidity. So for example, trichloroacetic acid (three -Cl groups) is a stronger acid than lactic acid (one -OH group) which in turn is stronger than acetic acid (no helping group). Hydroxide is a functional group consisting of oxygen and hydrogen: -O−H It has a charge of 1-. The term hydroxyl group is used when the functional group -OH is counted as a substituent of an organic compound. ... The chloride ion is formed when the element chlorine picks up one electron to form the negatively charged ion Cl−. The salts of hydrochloric acid HCl are also called chlorides. ... In organic chemistry, the chloroethanoic acids (trivial name chloroacetic acids) are three related chlorocarbon carboxylic acids: chloroethanoic acid (chloroacetic acid), CH2ClCOOH dichloroethanoic acid (dichloroacetic acid), CHCl2COOH trichloroethanoic acid (trichloroacetic acid), CCl3COOH As the number of chlorine atoms increases, the electronegativity of that end of the molecule increases, and the molecule... Lactic acid is a chemical compound that plays a role in several biochemical processes. ... The chemical compound acetic acid (from the Latin word acetum, meaning vinegar), systematically called ethanoic acid, is the acid that gives vinegar its sour taste. ...

Reactions

Carboxylic acids can be made by the complete oxidation of primary alcohols. This can be done with sodium dichromate, Sulphuric acid and heat. The most fundamental reactions in chemistry are the redox processes. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ...

Carboxylic acids react with bases to form carboxylate salts, in which the hydrogen of the -OH group is replaced with a metal ion. Thus, ethanoic acid (the same as acetic acid) reacts with sodium bicarbonate (baking soda) to form sodium ethanoate (sodium acetate), carbon dioxide, and water: The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... ion (disambiguation) An ion is an atom or group of atoms with a net electric charge. ... Sodium bicarbonate (NaHCO3), or sodium hydrogen carbonate, also known as baking soda and bicarbonate of soda, is a soluble white anhydrous or crystalline compound, with a slight alkaline taste resembling that of sodium carbonate. ... Carbon dioxide is an atmospheric gas composed of one carbon and two oxygen atoms. ...

CH₃COOH + NaHCO₃ → CH₃COONa + CO₂ + H₂O

Carboxyl groups also react with amine groups to form peptide bonds and with alcohols to form esters. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... Diagram showing the π-bonded amino acids and the point of rotation A peptide bond is a chemical bond formed between two molecules when the carboxyl group of one molecule reacts with the amino group of the other molecule, releasing a molecule of water (H2O). ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... For the Biblical Ester, see Esther. ...

Carboxylic acids react with Sulfonyl dichloride (SO₂Cl₂) to form acyl chlorides these are extremely reactive and useful to synthesise other organic compounds.

Carboxylic acids can be reduced by LiAlH₄ to form primary alcohols: Reduction or reducing has several meanings: In mathematics, reduction is the process of manipulating a series of equations or matrices into a desired simpler format. ... Lithium aluminum hydride (LiAlH4, commonly abbreviated to LAH) is a powerful reducing agent used in organic chemistry. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ...

Chemical reaction of the reduction of a carboxylic acid to a primary alcohol by LAH. Drawn by User:Diberri in ChemSketch. ...

Examples

Some carboxylic acids include:

• HCOOH formic acid (found in insect stings, formic refers to ants)
• all fatty acids, where R is an alkane in saturated acids and an alkene in unsaturated acids
  • CH₃COOH acetic or ethanoic acid (found in vinegar)
  • CH₃CH₂COOH propanoic acid
  • C₆H₅COOH benzoic acid (sodium benzoate, the sodium salt of benzoic acid is used as a food preservative)
  • butyric acid
  • CH₂=CHCOOH acrylic acid
• lactic acid, found in sour milk
• oxalic acid
• malonic acid
• succinic acid
• glutaric acid
• adipic acid
• salicylic acid
• all amino acids

Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... There are multiple topics for Ant or ANT: Ant: the insect River Ant: in Norfolk, England Apache Ant: a Java-based computer software system for builds Langtons ant: a two-dimensional Turing machine with a very simple set of rules, invented by Chris Langton. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... An alkane in organic chemistry is a type of hydrocarbon in which the molecule has the maximum possible number of hydrogen atoms and so has no double bonds (they are saturated). ... An alkene is one of the three classes of unsaturated hydrocarbons that contain at least one carbon- carbon double bond and have the general molecular formula of CnH2n (the other two being alkynes and arenes). ... The chemical compound acetic acid (from the Latin word acetum, meaning vinegar), systematically called ethanoic acid, is the acid that gives vinegar its sour taste. ... Vinegar (from Old French vinaigre sour wine) is a sour liquid made from the oxidation of ethanol in wine, cider, beer, or the like. ... The chemical compound propionic acid (systematically named propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. In the pure state, it is a colorless, corrosive liquid with a sharp, somewhat unpleasant odor. ... Structural formula Benzoic acid, C6H5C(O)OH, is an aromatic carboxylic acid. ... n-Butyric acid, IUPAC name n_Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2_COOH. It is notably found in rancid butter, parmesan cheese, or vomit and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... Acrylic acid or 2-propenoic acid is a chemical compound with the formula C3H4O2 and structure H H C = C _ C = O H OH (which is sometimes abbreviated as CH2=CHCOOH). ... Lactic acid is a chemical compound that plays a role in several biochemical processes. ... Oxalic acid ( IUPAC name: ethanedioic acid) is a bi- carboxylic acid with structure ( HOOC)-(COOH). ... Malonic acid is the bi-carboxylic acid with structure CH2(COOH)2. ... The acid succinic acid has the formula: HOOC-CH2-CH2-COOH At room temperature, pure succinic acid is a solid that forms colorless, odorless prisms. ... Adipic acid, (E-number E205) is a white crystalline powder appearing as an acid in aquaeous circumstances, though it is not highly soluble. ... Salicylic acid is a colorless, crystalline organic carboxylic acid. ... In chemistry, an amino acid is any molecule that contains both amino and carboxylic acid functional groups. ...

See also

• acid anhydride
• ester