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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 ...
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 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.
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.
Conversion and its related terms yield and selectivity are important terms in chemical reaction engineering.They are described as ratios of how much of a reactant has reacted (X — conversion, normally between zero and one), how much of a desired product was formed (Y — yield, normally also between zero and one) and how much desired product was formed in ratio to the undesired product(s) (S ...
Any non-tertiary benzylic alkyl group will be oxidized to a carboxyl group by aqueous potassium permanganate (KMnO 4) or concentrated nitric acid (HNO 3): (ArCHR 2 → ArCOOH). [6] Finally, the complex of chromium trioxide and 3,5-dimethylpyrazole (CrO 3 −dmpyz) will selectively oxidize a benzylic methylene group to a carbonyl: (ArCH 2 R → ...
In organic chemistry, the benzoin addition is an addition reaction involving two aldehydes (−CH=O). The reaction generally occurs between aromatic aldehydes or glyoxals (OCH=CHO), [1] [2] and results in formation of an acyloin (−C(O)CH(OH)−). In the classic example, benzaldehyde is converted to benzoin (PhCH(OH)C(O)Ph). [3]
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.