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The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid. [1] [2]
Isobutyraldehyde is the chemical compound with the formula (CH 3) 2 CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). [1] Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizzaro reaction even though it has alpha ...
Pentaerythritol was first reported in 1891 by German chemist Bernhard Tollens and his student P. Wigand. [5] It may be prepared via a base-catalyzed multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product plus formate ion.
Stanislao Cannizzaro FRS (/ ˌ k æ n ɪ ˈ z ɑːr oʊ / KAN-iz-AR-oh, [1] also US: /-ɪ t ˈ s ɑːr-/-it-SAR-, [2] Italian: [staniˈzlaːo kannitˈtsaːro]; 13 July 1826 – 10 May 1910) was an Italian chemist. He is famous for the Cannizzaro reaction and for his influential role in the atomic-weight deliberations of the Karlsruhe ...
Fermentation reactions can also be considered as disproportionation or dismutation biochemical reactions. Indeed, the donor and acceptor of electrons in the redox reactions supplying the chemical energy in these complex biochemical systems are the same organic molecules simultaneously acting as reductant or oxidant.
Cannizzaro's chemical interests had originally centered on natural products and on reactions of aromatic compounds; in 1853 he discovered that when benzaldehyde is treated with concentrated base, both benzoic acid and benzyl alcohol are produced—a phenomenon known today as the Cannizzaro reaction. In his 1858 pamphlet, Cannizzaro showed that ...
The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction. [1] [2] [3] 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 reaction exhibits an induction period, during which only the nonproductive Cannizzaro disproportionation of formaldehyde (to methanol and formate) occurs. The initial dimerization of formaldehyde to give glycolaldehyde ( 1 ) occurs via an unknown mechanism, possibly promoted by light or through a free radical process and is very slow.