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A classic organic reaction of benzil is the benzilic acid rearrangement, in which base catalyses the conversion of benzil to benzilic acid. This reactivity is exploited in the preparation of the drug phenytoin. Benzil also reacts with 1,3-diphenylacetone in an aldol condensation to give tetraphenylcyclopentadienone.
Benzilic acid can be prepared by heating a mixture of benzil, ethanol, and potassium hydroxide. 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.
A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift [1] is an organic reaction where a substituent moves from one atom to another atom in a chemical compound.
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. First performed by Justus von Liebig in 1838, [1] it is the first reported example of a rearrangement ...
In organic chemistry, an electrocyclic reaction is a type of pericyclic, rearrangement reaction where the net result is one pi bond being converted into one sigma bond or vice versa. [1] These reactions are usually categorized by the following criteria: Reactions can be either photochemical or thermal.
Benzilic acid rearrangement; Benzoin condensation; Bergman cyclization; Bergmann azlactone peptide synthesis; Bergmann degradation; Bergmann–Zervas carbobenzoxy method; Bernthsen acridine synthesis; Bestmann's reagent; Betti reaction; Biginelli pyrimidine synthesis; Biginelli reaction; Bingel reaction; Birch reduction; Bischler–Möhlau ...
Allylic shifts become the dominant reaction pathway when there is substantial resistance to a normal (non-allylic) substitution. For nucleophilic substitution, such resistance is known when there is substantial steric hindrance at or around the leaving group, or if there is a geminal substituent destabilizing an accumulation of positive charge.
In physical organic chemistry, the Grunwald–Winstein equation is a linear free energy relationship between relative rate constants and the ionizing power of various solvent systems, describing the effect of solvent as nucleophile on different substrates.