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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.
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 ...
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 ...
The reaction requires a strong Brønsted base and a weak Lewis acid, and gives a methanol coproduct: [1] (H 2 CO) 2 n + n B + n LA + n HArOH → n HC(=O)ArOH + n [HB][LA:OMe] Formally, it combines the Cannizzaro disproportionation with a directed Friedel-Crafts acylation .
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.
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 ...
Algar–Flynn–Oyamada reaction; Alkylimino-de-oxo-bisubstitution; Alkyne trimerisation; Alkyne zipper reaction; Allan–Robinson reaction; Allylic rearrangement; Amadori rearrangement; Amine alkylation; Angeli–Rimini reaction; Andrussov oxidation; Appel reaction; Arbuzov reaction, Arbusow reaction; Arens–Van Dorp synthesis, Isler ...
For laboratory use, Grignard reaction of phenylmagnesium bromide (C 6 H 5 MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol. The latter also gives benzoic acid, an example of an organic disproportionation reaction.