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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 ...
It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Benzyl alcohol is toxic to neonates and is associated with the gasping syndrome.
Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone. Cyclohexanone is an important precursor to some nylons. [8] Starting with the alkylation of benzene with mixture of 1 and 2-butenes, the cumene process produces phenol and butanones. [5]
In the body, benzene is enzymatically converted to a series of oxidation products including muconic acid, phenylmercapturic acid, phenol, catechol, hydroquinone and 1,2,4-trihydroxybenzene. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of ...
Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic acid (it takes two aldehydes to produce one acid and one alcohol). [5] This can be economically viable if the products can be separated and both have a value; the commercial conversion of furfural into furfuryl alcohol and 2-furoic acid is an example of this ...
The reaction can be extended to aliphatic aldehydes with base catalysis in the presence of thiazolium salts; the reaction mechanism is essentially the same.These compounds are important in the synthesis of heterocyclic compounds.
The starting point for the collection of the substituent constants is a chemical equilibrium for which the substituent constant is arbitrarily set to 0 and the reaction constant is set to 1: the deprotonation of benzoic acid or benzene carboxylic acid (R and R' both H) in water at 25 °C. Scheme 1. Dissociation of benzoic acids
When ortho substitution occurs in benzoic acid, steric hindrance causes the carboxyl group to twist out of the plane of the benzene ring. The twisting inhibits the resonance of the carboxyl group with the phenyl ring, leading to increased acidity of the carboxyl group.