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This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, [1] it is the first reported example of a rearrangement reaction. [2] It has become a classic reaction in organic synthesis and has been reviewed many times before.
Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction. [ 2 ] Uses
The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2. None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of reaction ...
Benzyl bromide is an organic compound with the formula C 6 H 5 CH 2 Br. The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties.
Benzylpotassium is an organopotassium compound with the formula C 6 H 5 CH 2 K, an orange powder. Like organo-alkali metal reagents in general, benzyl potassium is highly reactive, so much so that it reacts with most solvents. It is highly air sensitive.
The reaction constant, or sensitivity constant, ρ, describes the susceptibility of the reaction to substituents, compared to the ionization of benzoic acid. It is equivalent to the slope of the Hammett plot. Information on the reaction and the associated mechanism can be obtained based on the value obtained for ρ. If the value of:
Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C 6 H 5 CH 2 OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor.
Benzil (i.e. Bz 2, systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula (C 6 H 5 CO) 2, generally abbreviated (PhCO) 2. This yellow solid is one of the most common diketones. Its main use is as a photoinitiator in polymer chemistry. [4]