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Encyclopedia > Hydrolysis

Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water.[1][2] This is the type of reaction that is used to break down polymers. Water is added in this reaction. For other uses, see Chemical reaction (disambiguation). ... Look up chemical compound in Wiktionary, the free dictionary. ... H2O and HOH redirect here. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ...


In organic chemistry, hydrolysis can be considered as the reverse or opposite of condensation, a reaction in which two molecular fragments are joined for each water molecule produced. As hydrolysis may be a reversible reaction, condensation and hydrolysis can take place at the same time, with the position of equilibrium determining the amount of each product. Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. ...


In inorganic chemistry, the word is often applied to solutions of salts and the reactions by which they are converted to new ionic species or to precipitates (oxides, hydroxides, or salts). The addition of a molecule of water to a chemical compound, without forming any other products is usually known as hydration, rather than hydrolysis. Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group (OH-) and a hydrogen cation (an acidic proton) are added to the two carbon atoms bonded together in the carbon-carbon double bond which makes up an alkene functional group. ...


In biochemistry, hydrolysis is considered the reverse or opposite of dehydration synthesis. In hydrolysis, a water molecule (H2O), is added. Where as in dehydration synthesis, a molecule of water is removed. Biochemistry (from Greek: , bios, life and Egyptian kēme, earth[1]) is the study of the chemical processes in living organisms. ... Dehydration synthesis is a type of synthesis reaction in which two smaller molecules are joined together by a covalent bond and water is formed (released) in the reaction. ...

Contents

Examples

Hydrolysis of metal salts

Many metal ions are strong Lewis acids, and in water they may undergo hydrolysis to form basic salts. Such salts contain a hydroxyl group that is directly bound to the metal ion in place of a water ligand. For example, aluminium chloride undergoes extensive hydrolysis in water, such that the solution becomes quite acidic. In chemistry, a Lewis acid can accept a pair of electrons and form a coordinate covalent bond, after the American chemist Gilbert Lewis. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ...

This means that if solutions of AlCl3 are evaporated, hydrogen chloride is lost and the residue is a basic salt (in this case an oxychloride) in place of AlCl3. Such behaviour is also seen with other metal chlorides such as ZnCl2, SnCl2, FeCl3 and lanthanide halides such as DyCl3. With some compounds such as TiCl4, the hydrolysis may go to completion and form the pure hydroxide or oxide, in this case TiO2. R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... Zinc chloride (ZnCl2) is a colorless or white compound of zinc and chlorine that is extremely hygroscopic. ... Tin(II) chloride (stannous chloride) is a white crystalline solid with the formula SnCl2. ... R-phrases , S-phrases , Related Compounds Other anions Iron(III) fluoride Iron(III) bromide Other cations Iron(II) chloride Manganese(II) chloride Cobalt(II) chloride Ruthenium(III) chloride Related coagulants Iron(II) sulfate Polyaluminium chloride Except where noted otherwise, data are given for materials in their standard state (at 25... Dysprosium(III) chloride (DyCl3), also known as dysprosium trichloride, is a compound of dysprosium and chlorine. ... Titanium tetrachloride (or titanium(IV) chloride) is the chemical compound with the formla TiCl4. ... Hydroxide is a polyatomic ion consisting of oxygen and hydrogen: OH− It has a charge of −1. ... An oxide is a chemical compound containing at least one oxygen atom and other elements. ... Titanium dioxide, also known as titanium(IV) oxide or titania, is the naturally occurring oxide of titanium, chemical formula TiO2. ...


Hydrolysis of an ester link

In a hydrolysis reaction that involves breaking an ester link, one hydrolysis product contains a hydroxyl functional group, while the other contains a carboxylic acid functional group. For other uses, see Ester (disambiguation). ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted...


The carbonyl is attacked by a hydroxide anion (or a water molecule, which is rapidly deprotonated). The resulting tetrahedral intermediate breaks down. The alkoxide fragment breaks off from the tetrahedral carbon and becomes an alcohol by protonation, leaving the acyl fragment with the attacking hydroxide, to produce a carboxylic acid. This is the reverse of the esterification reaction, yielding the original alcohol and carboxylic acid again. In a basic solution, the carboxylic acid is deprotonated, such that the basic hydrolysis is irreversible, while acidic hydrolysis is not. The general structure of a tetrahedral molecule, with the central atom labelled pink. ... This article does not cite any references or sources. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted...


There are two main methods for hydrolysing esters, basic hydrolysis and acid-catalysed. With acid-catalysed hydrolysis a dilute acid is used to protonate the carbonyl group in order to activate it towards nucleophilic attack by a water molecule. However the more usual method for ester hydrolysis involves refluxing the ester with an aqueous base such as NaOH or KOH. Once the reaction is complete, the carboxylate salt is acidified to release the free carboxylic acid. Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit In... For other uses, see Acid (disambiguation). ... It has been suggested that this article or section be merged into Catalysis. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... Diagram of typical reflux apparatus. ... Flash point Non-flammable. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... 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. ...

Basic hydrolysis of an ester

An important example of this reaction is the release of fatty acids from glycerol in triglyceride hydrolysis, as occurs during saponification. Shortened length of Ester_Hydrolysis. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Glycerin, also well known as glycerine and glycerol, and less commonly as 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... Example of an unsaturated fat triglyceride. ... Saponification of a lipid with potassium hydroxide. ...


Hydrolysis of amide links

In other hydrolysis reactions, such as hydrolysis of an amide link into a carboxylic acid and an amine product or ammonia, only the carboxylic acid product has a hydroxyl group derived from the water. The amine product (or ammonia) gains the remaining hydrogen ion. A more specific case of the hydrolysis of an amide link is hydrolyzing the peptide links of amino acids. Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... For other uses, see Ammonia (disambiguation). ... 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). ... This article is about the class of chemicals. ...


Hydrolysis of cellulose (Cellulolysis)

Main article: Cellulase

Cellulolytic is relating to or causing the hydrolysis of cellulose (i.e. cellulolytic bacteria, fungi or enzymes). Cellulase is an enzyme complex which breaks down cellulose to beta-glucose. ... Cellulose as polymer of β-D-glucose Cellulose in 3D Cellulose (C6H10O5)n is a polysaccharide of beta-glucose. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ...


The hydrolysis into glucose (i.e. of cellulose or starch) is called saccharification.


Irreversibility of hydrolysis under physiological conditions

Under physiological conditions (i.e. in dilute aqueous solution), a hydrolytic cleavage reaction, where the concentration of a metabolic precursor is low (on the order of 10-3 to 10-6 molar), is essentially thermodynamically irreversible. To give an example: Thermodynamics (from the Greek θερμη, therme, meaning heat and δυναμις, dynamis, meaning power) is a branch of physics that studies the effects of changes in temperature, pressure, and volume on physical systems at the macroscopic scale by analyzing the collective motion of their particles using statistics. ...

A + H2O → X + Y

Assuming that x is the final concentration of products, and that C is the initial concentration of A, and W = [H2O] = 55.5 molar, then x can be calculated with the equation:

let Kd×W = k:


then


For a value of C = 0.001 molar, and k = 1 molar, x/C > 0.999. Less than 0.1% of the original reactant would be present once the reaction is complete.


This theme of physiological irreversibility of hydrolysis is used consistently in metabolic pathways, since many biological processes are driven by the cleavage of anhydrous pyrophosphate bonds. Structure of anhydride. ... In chemistry, the anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. ...


See also

Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Dehydration synthesis is a type of synthesis reaction in which two smaller molecules are joined together by a covalent bond and water is formed (released) in the reaction. ... In organic chemistry, solvolysis is a special type of nucleophilic substitution where the nucleophile is a solvent molecule. ...

References

  1. ^ Compendium of Chemical Terminology, hydrolysis, accessed 2007-01-23.
  2. ^ Compendium of Chemical Terminology, solvolysis, accessed 2007-01-23.

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