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Homologation Reactions
In organic chemistry, a homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series. A homologous series is a group of compounds that differ by a constant unit, generally a methylene () group. The reactants undergo a homologation when the number of a repeated structural unit in the molecules is increased. The most common homologation reactions increase the number of methylene () units in saturated chain within the molecule. For example, the reaction of aldehydes or ketones with diazomethane or methoxymethylenetriphenylphosphine to give the next homologue in the series. Examples of homologation reactions include: * Kiliani-Fischer synthesis, where an aldose molecule is elongated through a three-step process consisting of: *# Nucleophillic addition of cyanide to the carbonyl to form a cyanohydrin *# Hydrolysis to form a lactone *# Reduction to form the homologous aldose * Wittig reaction ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes Physical property, physical and Chemical property, chemical properties, and evaluation of Reactivity (chemistry), chemical reactivity to understand their behavior. The study of organic reactions includes the organic synthesis, chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. The range of chemicals studied chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but a ...
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Arndt–Eistert Reaction
In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. It is named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978). The method entails treating an acid chloride with diazomethane. It is a popular method of producing β-amino acids from α-amino acids. Conditions Aside from the acid chloride substrate, three reagents are required: diazomethane, water, and a metal catalyst. Each has been well investigated. The diazomethane is required in excess so as to react with the HCl formed previously. Not taking diazomethane in excess results in HCl reacting with the diazoketone to form chloromethyl ketone and N2. Mild conditions allow this reaction to take place while not affecting complex or reducible groups in the reactant-acid. The reaction requires the presence of a nucleophile (water). A metal catalyst is required. Usually Ag2O is chosen but other metals and even light effect the rea ...
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Organic Reduction
Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carry the name but do not actually involve electron transfer.March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. Instead the relevant criterion for organic oxidation is gain of oxygen and/or loss of hydrogen.''Organic Redox Systems: Synthesis, Properties, and Applications'', Tohru Nishinaga 2016 Simple functional groups can be arranged in order of increasing oxidation state. The oxidation numbers are only an approximation: When methane is oxidized to carbon dioxide its oxidation number changes from −4 to +4. Classical reductions include alkene reduction to alkanes and classical oxidations include oxidation of alcohols to aldehydes. In oxidations electrons ...
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Hydrochloric Acid
Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical. Etymology Because it was produced from halite, rock salt according to the methods of Johann Rudolph Glauber, hydrochloric acid was historically called by European alchemists ''spirits of salt'' or ''acidum salis'' (salt acid). Both names are still used, especially in other languages, such as , , , , , , , , , , (''ensan''), zh, 盐酸 (''yánsuān''), and (''yeomsan''). Gaseous HCl was called ''marine acid air''. The name ''muriatic acid'' has the same origin (''muriatic'' means "pertaining to brine or salt", hence ''muriate'' means hydrochloride), and this ...
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Thionyl Chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagent, with approximately per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also List of Schedule 3 substances (CWC), listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons. Thionyl chloride is sometimes confused with sulfuryl chloride, , but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. Production The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride. This synthesis can be adapted to the laboratory by heating oleum to slowly distill the sulfur trioxide into a cooled fla ...
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Acid Chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example of an acyl chloride is acetyl chloride, . Acyl chlorides are the most important subset of acyl halides. Nomenclature Where the acyl chloride Moiety (chemistry), moiety takes priority, acyl chlorides are named by taking the name of the parent carboxylic acid, and substituting ''-yl chloride'' for ''-ic acid''. Thus: : : :Butyric acid, butyr''ic acid'' (C3H7COOH) → Butyryl chloride, butyr''yl chloride'' (C3H7COCl) (Idiosyncratically, for some trivial names, ''-oyl chloride'' substitutes ''-ic acid''. For example, pival''ic acid'' becomes pival''oyl chloride'' and acryl''ic acid'' becomes acryl''oyl chloride.'' The names pivalyl chloride and acrylyl chloride are less commonly used, although they are arguably more logical.) When other fu ...
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Bile Acid
Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver in peroxisomes. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary bile acids are those synthesized by the liver. Secondary bile acids result from bacterial actions in the colon. In humans, taurocholic acid and glycocholic acid (derivatives of cholic acid) and taurochenodeoxycholic acid and glycochenodeoxycholic acid (derivatives of chenodeoxycholic acid) are the major bile salts. The salts of their 7-alpha-dehydroxylated derivatives, deoxycholic acid and lithocholic acid, are also found, with derivatives of cholic, chenodeoxycholic and deoxycholic acids accounting for over 90% of human biliary bile acids. Description Bile acids comprise about 80% of the organic compounds in bile (others are phospholipids and cholesterol). An increased secretion of bile acids produces an increase ...
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Carboxylic Acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), 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. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They often have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid () is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named ...
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Pyruvic Acid
Pyruvic acid (CH3COCOOH) is the simplest of the keto acids, alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate acid, conjugate base, CH3COCOO−, is an metabolic intermediate, intermediate in several metabolic pathways throughout the cell. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or converted to fatty acids through a reaction with acetyl-CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation. Pyruvic acid supplies energy to cell (biology), cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively lactic acid fermentation, ferments to produce lactic acid, lactate when oxygen is lacking. Chemistry In 1834, Théophile-Jules Pelouze distilled tartaric acid and isolated glutaric acid and another unknown organi ...
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Gallagher–Hollander Degradation
In the Gallagher–Hollander degradation (1946) pyruvic acid is removed from a linear aliphatic carboxylic acid yielding a new acid with two carbon atoms fewer.Vincent P. Hollander and T. F. Gallagher PArtial synthesis of compounds related to adrenal cortical hormones. VII. degradation of the side chain of cholanic acid ''J. Biol. Chem.'', Mar 1946; 162: 549–5Link The original publication concerns the conversion of bile acid in a series of reactions: acid chloride (2) formation with thionyl chloride, diazoketone formation (3) with diazomethane, chloromethyl ketone formation (4) with hydrochloric acid, organic reduction of chlorine to methylketone (5), ketone halogenation to 6, elimination reaction with pyridine to enone 7 and finally oxidation with chromium trioxide Chromium trioxide (also known as chromium(VI) oxide or chromic anhydride) is an inorganic compound with the formula . It is the acidic anhydride of chromic acid, and is sometimes marketed under the same name. Th ...
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DeMayo Reaction
The DeMayo reaction is a photochemical reaction in which the enol of a 1,3-diketone reacts with an alkene (or another species with a C=C bond) and the resulting cyclobutane ring undergoes a retro-aldol reaction to yield a 1,5-diketone: The net effect is to add the two carbon atoms in the C=C double bond between the two carbonyl groups of the diketone. It is thus useful in syntheses both as a relatively selective way to join two parts of a molecule and as a way to apply the more developed chemistry of 1,3-diketone synthesis to 1,5-diketones. The first part is a [2+2] cycloaddition. The ensuing retro-aldol cleavage is favored by the relative instability of the cyclobutane ring. References

{{Reflist Organic reactions Name reactions ...
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