Claisen–Schmidt Condensation
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Claisen–Schmidt Condensation
In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen. It can be considered as a specific variation of the aldol condensation. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J. Gustav Schmidt, who independently published on this topic in 1880 and 1881. An example is the synthesis of dibenzylideneacetone ((1''E'', 4''E'')-1,5-diphenylpenta-1,4-dien-3-one). : Quantitative yields in Claisen–Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus benzaldehydes Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. It is a colorless liquid with a characteristic almond-like odor ....{{cite journal , doi = 10.3390/molecules17010571 , ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and 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 and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the 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 in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ...
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Aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The C=O bond length is about 120-122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors. Al ...
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Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ...
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α-hydrogen
In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of numeric prefixes to indicate the position of substituents, generally by identifying the parent hydrocarbon chain and assigning the carbon atoms based on their substituents in order of precedence. For example, there are at least two isomers of the linear form of pentanone, a ketone that contains a chain of exactly five carbon atoms. There is an oxygen atom bonded to one of the middle three carbons (if it were bonded to an end carbon, the molecule would be an aldehyde, not a ketone), but it is not clear where it is located. In this example, the carbon atoms are numbered from one to five, which starts at one end and proceeds sequentially along the chain. Now the position of the oxygen atom can be defined as on carbon atom number two, three or ...
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Aldol Condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone. The overall reaction is as follows (where the Rs can be H): Aldol condensations are important in organic synthesis and biochemistry as ways to form carbon–carbon bonds. In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals. The term ''aldol condensation'' is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction itself—as catalyzed by aldolases. However, this is formally an addition reaction rather than a condensation reaction because it does not invo ...
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Rainer Ludwig Claisen
Rainer Ludwig Claisen (; 14 January 1851 – 5 January 1930) was a German chemist best known for his work with condensations of carbonyls and sigmatropic rearrangements. He was born in Cologne as the son of a jurist and studied chemistry at the university of Bonn (1869), where he became a member of K.St.V. Arminia. He served in the army as a nurse in 1870–1871 and continued his studies at Georg August University of Göttingen, Göttingen University. He returned to the University of Bonn in 1872 and started his academic career at the same university in 1874. He died in 1930 in Godesberg am Rhein (near Bonn The federal city of Bonn ( lat, Bonna) is a city on the banks of the Rhine in the German state of North Rhine-Westphalia, with a population of over 300,000. About south-southeast of Cologne, Bonn is in the southernmost part of the Rhine-Ru ...). Career Scientific contributions * Described the condensation of aromatic aldehydes with aliphatic aldehydes or ke ...
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Berichte Der Deutschen Chemischen Gesellschaft
''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with ''Recueil des Travaux Chimiques des Pays-Bas'' to form ''Chemische Berichte/Recueil'' in 1997. ''Chemische Berichte/Recueil'' was then merged with other European journals in 1998 to form ''European Journal of Inorganic Chemistry''. History Founded in 1868 as ''Berichte der Deutschen Chemischen Gesellschaft'' (, CODEN BDCGAS), it operated under this title until 1928 (Vol. 61). The journal was then split into: * ''Berichte der Deutschen Chemischen Gesellschaft, A: Vereins-Nachrichten'' (, CODEN BDCAAS), and * ''Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen'' (, CODEN BDCBAD). Vol. 78 and 79 (1945–1946) were omitted and not published due to World War II. The journal was renamed ''Chemische Berichte'' (, CODEN CHBEAM) in 19 ...
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Dibenzylideneacetone
Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. It was first prepared in 1881 by the German chemist Rainer Ludwig Claisen (1851–1930) and the Swiss chemist Charles-Claude-Alexandre Claparède (14 April 1858 – 1 November 1913). Preparation The ''trans'',''trans'' isomer can be prepared in high yield and purity by condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium followed by recrystallization. : This reaction, which proceeds via the intermediacy of benzylideneacetone, is often performed in organic chemistry classes, and is called Claisen-Schmidt condensation. Reactions and derivatives Prolonged exposure to sunlight initiates +2cycloadditions, converting it to a mixture of dimeric and trimeric cyclobutane cycloadducts. Uses Dibenzylideneacetone is used as a component in sunscreens and as a ligand ...
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Journal Of Chemical Education
The ''Journal of Chemical Education'' is a monthly peer-reviewed academic journal available in both print and electronic versions. It is published by the Division of Chemical Education of the American Chemical Society and was established in 1924 by Neil Gordon. The journal covers research on chemical education Chemistry education (or chemical education) is the study of teaching and learning chemistry. It is one subset of STEM education or discipline-based education research (DBER). Topics in chemistry education include understanding how students learn ..., and its target audience includes instructors of chemistry from middle school through graduate school and some scientists in commerce, industry, and government. References External links * Chemical education journals American Chemical Society academic journals Monthly journals Publications established in 1924 English-language journals {{chemistry-journal-stub ...
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Synthesis Dibenzylideneaceton
Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organic compounds ***Total synthesis, the complete organic synthesis of complex organic compounds, usually without the aid of biological processes ***Convergent synthesis or linear synthesis, a strategy to improve the efficiency of multi-step chemical syntheses **Dehydration synthesis, a chemical synthesis resulting in the loss of a water molecule *Biosynthesis, the creation of an organic compound in a living organism, usually aided by enzymes **Photosynthesis, a biochemical reaction using a carbon molecule to produce an organic molecule, using sunlight as a catalyst **Chemosynthesis, the synthesis of biological compounds into organic waste, using methane or an oxidized molecule as a catalyst **Amino acid synthesis, the synthesis of an amino acid ...
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Yield (chemistry)
In chemistry, yield, also referred to as reaction yield, is a measure of the quantity of Mole (unit), moles of a Product (chemistry), product formed in relation to the reactant consumed, obtained in a chemical reaction, usually expressed as a percentage. Yield is one of the primary factors that scientists must consider in organic synthesis, organic and inorganic chemical synthesis processes. In chemical reaction engineering, "yield", "Conversion (chemistry), conversion" and "selectivity" are terms used to describe ratios of how much of a reactant was consumed (conversion), how much desired product was formed (yield) in relation to the undesired product (selectivity), represented as X, Y, and S. Definitions In chemical reaction engineering, "yield", "Conversion (chemistry), conversion" and "selectivity" are terms used to describe ratios of how much of a reactant has reacted—conversion, how much of a desired product was formed—yield, and how much desired product was formed ...
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Sodium Hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali that decomposes proteins at ordinary ambient temperatures and may cause severe chemical burns. It is highly soluble in water, and readily absorbs moisture and carbon dioxide from the air. It forms a series of hydrates . The monohydrate crystallizes from water solutions between 12.3 and 61.8 Â°C. The commercially available "sodium hydroxide" is often this monohydrate, and published data may refer to it instead of the anhydrous compound. As one of the simplest hydroxides, sodium hydroxide is frequently used alongside neutral water and acidic hydrochloric acid to demonstrate the pH scale to chemistry students. Sodium hydroxide is used in many industries: in the manufacture of pulp and paper, textiles, drinking water, soaps and deterge ...
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