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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]
Usually, the crossed product is the major one. Any traces of the self-aldol product from the aldehyde may be disallowed by first preparing a mixture of a suitable base and the ketone and then adding the aldehyde slowly to the said reaction mixture. Using too concentrated base could lead to a competing Cannizzaro reaction. [12]
The dianion, methanediolate, is believed to be an intermediate in the crossed Cannizzaro reaction.. Gaseous methanediols can be generated by electron irradiation and sublimation of a mixture of methanol and oxygen ices.
Treatment of the aldehyde 2-ethylbutyraldehyde with formaldehyde and potassium hydroxide gives a crossed Cannizzaro reaction yielding prenderol. [7] See also
Crossover experiments allow for experimental study of a reaction mechanism. Mechanistic studies are of interest to theoretical and experimental chemists for a variety of reasons including prediction of stereochemical outcomes, optimization of reaction conditions for rate and selectivity, and design of improved catalysts for better turnover number, robustness, etc. [6] [7] Since a mechanism ...
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:
Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.
Neopentyl glycol is synthesized industrially by the aldol reaction of formaldehyde and isobutyraldehyde.This creates the intermediate hydroxypivaldehyde, which can be converted to neopentyl glycol by either a Cannizzaro reaction with excess formaldehyde, or by hydrogenation using palladium on carbon.