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]
Cannizzaro first accomplished this transformation in 1853, when he obtained benzyl alcohol and potassium benzoate from the treatment of benzaldehyde with potash (potassium carbonate). More typically, the reaction would be conducted with sodium hydroxide or potassium hydroxide, giving the sodium or potassium carboxylate salt of the carboxylic-acid product:
2 C6H5CHO + KOH → C6H5CH2OH + C6H5COOK
The process is a redox reaction involving transfer of a hydride from one substrate molecule to the other: one aldehyde is oxidized to form the acid, the other is reduced to form the alcohol.[3]
^Cannizzaro, S. (1853). "Ueber den der Benzoësäure entsprechenden Alkohol" [On the alcohol corresponding to benzoic acid]. Liebigs Annalen der Chemie und Pharmacie. 88: 129–130. doi:10.1002/jlac.18530880114.
^List, K.; Limpricht, H. (1854). "Ueber das sogenannte Benzoëoxyd und einige andere gepaarte Verbindungen" [On so-called benzoic oxide and some other paired compounds]. Liebigs Annalen der Chemie und Pharmacie. 90 (2): 190–210. doi:10.1002/jlac.18540900211.
^Geissman, T. A. "The Cannizzaro Reaction" Org. React.1944, 2, 94. doi:10.1002/0471264180.or002.03(Review)
and 29 Related for: Cannizzaro reaction information
The Cannizzaroreaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of...
famous for the Cannizzaroreaction and for his influential role in the atomic-weight deliberations of the Karlsruhe Congress in 1860. Cannizzaro was born in...
aluminium alkoxides are effective catalysts for the reaction. In the related Cannizzaroreaction, the base is sodium hydroxide and then the oxidation...
aldehyde slowly to the said reaction mixture. Using too concentrated base could lead to a competing Cannizzaroreaction. The Aldox process, developed...
for a base-catalyzed self-condensation (Cannizzaroreaction) to occur. A general scheme of the Cannizzaroreaction is depicted below. There have been a series...
for the reaction, consisting of the following steps: The reaction exhibits an induction period, during which only the nonproductive Cannizzaro disproportionation...
For laboratory use, Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde and the Cannizzaroreaction of benzaldehyde also give benzyl...
can still result in substantial byproducts. Examples include the Cannizzaroreaction, in which approximately 50% of the reactant aldehyde becomes the...
Cannizzaroreaction, an aldehyde is converted into an alcohol and a carboxylic acid. In the related Tishchenko reaction, the organic redox reaction product...
undergoes disproportionation upon treatment with concentrated alkali (Cannizzaroreaction): one molecule of the aldehyde is reduced to the benzyl alcohol and...
hydroxypivaldehyde, which can be converted to neopentyl glycol by either a Cannizzaroreaction with excess formaldehyde, or by hydrogenation using palladium on...
syn- or anti-1,3-diols. The resulting carbonyl is reduced using the Cannizzaroreaction or by catalytic hydrogenation: RC(O)CH3 + CH2O → RC(O)CH2CH2OH RC(O)CH2CH2OH...
(e.g., benzaldehyde), addition of strong base induces the Cannizzaroreaction. This reaction results in disproportionation, producing a mixture of alcohol...
hydrogenation catalyst then reduces to the alcohol. The Cannizzaroreaction is a competing reaction when two aldehyde molecules react by disproportionation...
pentaerythritol synthesis and in the crossed Cannizzaroreaction of formaldehyde with the aldol reaction product trimethylol acetaldehyde [3-hydroxy-2...
mainly of academic interest. Disproportionation of an aldehyde in the Cannizzaroreaction Rearrangement of diketones in the benzilic acid rearrangement Involving...
α-keto aldehydes can be transformed into α-hydroxy acids through the Cannizzaroreaction. R−C(O)CHO + 2OH− → R−CH(OH)CO−2 + H2O 2-Hydroxy-4-(methylthio)butyric...
m-phenoxytoluene over selenium dioxide provides m-phenoxybenzaldehyde. Third, a Cannizzaroreaction of the benzaldehyde in formaldehyde and potassium hydroxide affords...
methanol. In the Cannizzaroreaction, formaldehyde and base react to produce formic acid and methanol, a disproportionation reaction. Formaldehyde reacts...
H+ With concentrated base, glyoxylic acid disproportionates via a Cannizzaroreaction, forming hydroxyacetic acid and oxalic acid:[citation needed] 2 OCHCO2H...
multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaroreaction with a...
expansion of a cyclopentane to a cyclohexane ring as an example reaction. Cannizzaroreaction Pinacol rearrangement Liebig, J. (1838). "Ueber Laurent's Theorie...
hydrolysis, the Cannizzaroreaction, nucleophilic aliphatic substitution, nucleophilic aromatic substitution, and in elimination reactions. The reaction medium...
condensation reaction of propionaldehyde with formaldehyde: CH3CH2CHO + 2 CH2O → CH3C(CH2OH)2CHO The second step entails a Cannizzaroreaction: CH3C(CH2OH)2CHO...
methanediolate, is believed to be an intermediate in the crossed Cannizzaroreaction. Gaseous methanediols can be generated by electron irradiation and...