The Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide.^[1] The reaction product is an ester. Catalysts are aluminium alkoxydes or sodium alkoxides. Benzaldehyde reacts with sodium benzyloxide (generated from sodium and benzyl alcohol) to benzyl benzoate.^[2] Jump to: navigation, search A chemical reaction is a process involving one, two or more substances (called reactants), characterized by a chemical change and yielding one or more product(s) which are different from the reactants. ... jfkdjdfdfd--69. ... An aldehyde is either a functional group consisting of a terminal carbonyl group, or a compound containing a terminal carbonyl group. ... An alkoxide has an organic group bonded to a negatively charged oxygen atom, they are generally basic. ... In organic chemistry and biochemistry, esters are organic compounds where an organic group (symbolised by R in this article) replaces a hydrogen atom (or more than one) in an oxygen acid. ... A catalyst (Greek: καταλύτης, catalytēs) is a substance that accelerates the rate (speed) of a chemical reaction without itself being transformed or consumed by the reaction (see also catalysis). ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ...

Paraformaldehyde reacts with boric acid to methyl formate.^[3] The key step in the reaction mechanism for this reaction is a 1,3-hydride shift in the hemiacetal intermediate formed from two succesive nucleophilic addition reactions, the first one from the catalyst. The hydride shift regenerates the alkoxide catalyst. The chemical compound formaldehyde (also known as methanal), is a gas with a strong pungent smell. ... Boric acid, also called boracic acid or orthoboric acid, is a mild acid often used as an antiseptic, insecticide, flame retardant, and as a precursor of other chemical compounds. ... Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ... An overall description of how a reaction occurs. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ...

In the related Cannizzaro reaction the base is sodium hydroxide and then the oxidation product is a carboxylic acid and the reduction product is an alcohol. The Cannizzaro reaction named after Stanislao Cannizzaro is a chemical reaction that involves disproportionation of any aldehyde lacking a hydrogen atom in the alpha position, in the presence of a strong base. ... Jump to: navigation, search Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. The salts and anions of carboxylic acids are called carboxylates generally. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... 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). ...

Related reactions

• Aldol-Tishchenko reaction
• Baylis-Hillman reaction
• Cannizzaro reaction
• Meerwein-Ponndorf-Verley Reduction
• Oppenauer Oxidation

The Cannizzaro reaction named after Stanislao Cannizzaro is a chemical reaction that involves disproportionation of any aldehyde lacking a hydrogen atom in the alpha position, in the presence of a strong base. ...

References

1. ^  V. Tishchenko, J. Russ. Phys. Chem. Soc. 1906, 38, 355, 482, 540, 547.
2. ^  O. Kamm and W. F. Kamm Organic Syntheses, Coll. Vol. 1, p.104; Vol. 2, p.5 Online article
3. ^  Boric acid catalyzed Tishchenko reactions. Paul R. Stapp, J. Org. Chem. 1973, 38(7), 1433-1434. Abstract