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In the classic example, benzaldehyde is converted to benzoin (PhCH(OH)C(O)Ph). [3] The benzoin condensation was first reported in 1832 by Justus von Liebig and Friedrich Wöhler during their research on bitter almond oil. [4] The catalytic version of the reaction involving cyanide was developed by Nikolay Zinin in the late 1830s. [5] [6 ...
The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. [1] While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. [2]
For example, cyanide is a key catalyst in the benzoin condensation, a classical example of polarity inversion. Mechanism of the benzoin condensation The net result of the benzoin reaction is that a bond has been formed between two carbons that are normally electrophiles.
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.
With aromatic aldehydes such as benzaldehyde, the benzoin condensation is a competing reaction. The reaction is used in carbohydrate chemistry as a chain extension method for example that of D-xylose.
The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base.This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
Benzoin (/ ˈ b ɛ n z oʊ. ɪ n / or /-ɔɪ n /) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation.
In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen. It can be considered as a specific variation of the aldol condensation .