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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 ...
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 ...
Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation. Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic ...
The term "benzoyl" should not be confused with benzyl, which has the formula −CH 2 −C 6 H 5. The benzoyl group is given the symbol "Bz" whereas benzyl is commonly abbreviated "Bn". The benzoyl group is given the symbol "Bz" whereas benzyl is commonly abbreviated "Bn".
Benzyl chloride is an alkylating agent. Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride slowly reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid.
As with other acyl chlorides, it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride. It was first prepared by treatment of benzaldehyde with chlorine. [3] An early method for production of benzoyl chloride involved chlorination of benzyl alcohol. [4]
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. [2]
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.