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Bodroux–Chichibabin Aldehyde Synthesis
The Bodroux–Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer. : Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n- hexanal: : See also *Bouveault aldehyde synthesis The Bouveault aldehyde synthesis (also known as the Bouveault reaction) is a one-pot substitution reaction that replaces an alkyl or aryl halide with a formyl group using a ''N'',''N''-disubstituted formamide. For primary alkyl halides this produc ... References * * * * * {{DEFAULTSORT:Bodroux-Chichibabin aldehyde synthesis Carbon-carbon bond forming reactions Name reactions Formylation reactions ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reaction
The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of carbon–carbon bonds. The reaction of an organic halide with magnesium is ''not'' a Grignard reaction, but provides a Grignard reagent. : Grignard reactions and reagents were discovered by and are named after the French chemist François Auguste Victor Grignard ( University of Nancy, France), who published it in 1900 and was awarded the 1912 Nobel Prize in Chemistry for this work. Reaction mechanism Because carbon is more electronegative than magnesium, the carbon attached to magnesium functions as a nucleophile and attacks the electrophilic carbon atom that is present within the polar bond of a carbonyl group. The addition of the Grignard reagent to the carbonyl typically proceeds through a six-membered ring transition state. Based ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triethyl Orthoformate
Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. This colorless volatile liquid, the orthoester of formic acid, is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol. It may also be prepared from the reaction of sodium ethoxide, formed in-situ from sodium and absolute ethanol, and chloroform: : CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + H2 + 3 NaCl Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis, for example: : RMgBr + HC(OC2H5)3 → RC(H)(OC2H5)2 + MgBr(OC2H5) : RC(H)(OC2H5)2 + H2O → RCHO + 2 C2H5OH In coordination chemistry, it is used to convert metal aquo complexes to the corresponding ethanol complexes: : i(H2O)6BF4)2 + 6 HC(OC2H5)3 → i(C2H5OH)6BF4)2 + 6 HC(O)(OC2H5) + 6 HOC2H5 Triethyl orthoformate (TEOF) is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Such carboxylic acids, refluxed neat in excess TEOF until low-boil ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetal
In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry. The term ketal is sometimes used to identify structures associated with ketones (both R groups organic fragments rather than hydrogen) rather than aldehydes and, historically, the term acetal was used specifically for the aldehyde-related cases (having at least one hydrogen in place of an R on ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrolyzed
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and water molecule to split into two parts. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexanal
Hexanal, also called hexanaldehyde or caproaldehyde is an alkyl aldehyde used in the flavor industry to produce fruity flavors. Its scent resembles freshly cut grass Poaceae () or Gramineae () is a large and nearly ubiquitous family of monocotyledonous flowering plants commonly known as grasses. It includes the cereal grasses, bamboos and the grasses of natural grassland and species cultivated in lawns a ..., like ''cis''-3-hexenal. It is potentially useful as a natural extract that prevents fruit spoilage. It occurs naturally, and contributes to a hay-like "off-note" flavor in green peas. The first synthesis of hexanal was published in 1907 by P. Bagard. / American Chemical Society References [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bouveault Aldehyde Synthesis
The Bouveault aldehyde synthesis (also known as the Bouveault reaction) is a one-pot substitution reaction that replaces an alkyl or aryl halide with a formyl group using a ''N'',''N''-disubstituted formamide. For primary alkyl halides this produces the homologous aldehyde one carbon longer. For aryl halides this produces the corresponding carbaldehyde. The Bouveault aldehyde synthesis is an example of a formylation reaction, and is named for French scientist Louis Bouveault. : Reaction mechanism The first step of the Bouveault aldehyde synthesis is the formation of the Grignard reagent. Upon addition of a ''N'',''N''-disubstituted formamide (such as dimethylformamide) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde. Variations Variants using organolithium reagents instead of magnesium-based Grignard reagents are also considered Bouveault aldehyde syntheses.Jie Jack Li. ''Name Reactions: A Collection of Detailed Reaction Mechanisms''. Springer ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemische Berichte
''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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
