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The Birch reduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes.The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally liquid ammonia) with an alkali metal (traditionally sodium) and a proton source (traditionally an alcohol).
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 ...
A specialized use of sodium-ammonia solutions is the Birch reduction. Other reactions where sodium is used as a reducing agent also are assumed to involve solvated electrons, e.g. the use of sodium in ethanol as in the Bouveault–Blanc reduction.
A weak acid cannot always be neutralized by a weak base, and vice versa. However, for the neutralization of benzoic acid (K a,A = 6.5 × 10 −5) with ammonia (K a,B = 5.6 × 10 −10 for ammonium), K = 1.2 × 10 5 >> 1, and more than 99% of the benzoic acid is converted to benzoate.
Arthur John Birch, AC CMG FRS FAA (3 August 1915 – 8 December 1995) was an Australian organic chemist. [1] [2] [3] [4]Birch developed the Birch reduction of aromatic rings (by treatment with lithium metal and ammonia) which is widely used in synthetic organic chemistry.
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, 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)−).
This intermediate collapses with the elimination of the azo group to yield an aryldiazene with an ortho carboxylate group, which extrudes nitrogen gas to afford the anionic form of the observed benzoic acid product, presumably through the generation and immediate protonation of an aryl anion intermediate. The product is isolated upon acidic workup.