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The mechanism of acid-catalyzed hydrolysis of esters is the reverse of Fischer esterification. Acid is only required in catalytic amounts, as in Fischer esterification, and an excess of water drives the equilibrium towards carboxylic acid and alcohol. [1]
In acid-catalyzed Fischer esterification, the proton binds to oxygens and functions as a Lewis acid to activate the ester carbonyl (top row) as an electrophile, and converts the hydroxyl into the good leaving group water (bottom left). Both lower the kinetic barrier and speed up the attainment of chemical equilibrium.
The hydrolysis of esters can occur through either acid and base catalyzed mechanisms, both of which proceed through a tetrahedral intermediate. In the base catalyzed mechanism the reactant goes from a neutral species to negatively charged intermediate in the rate determining (slow) step , while in the acid catalyzed mechanism a positively ...
Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. [1] Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile.
Two common modes of Lewis acid catalysis in reactions with polar mechanisms. In reactions with polar mechanisms, Lewis acid catalysis often involves binding of the catalyst to Lewis basic heteroatoms and withdrawing electron density, which in turn facilitates heterolytic bond cleavage (in the case of Friedel-Crafts reaction) or directly activates the substrate toward nucleophilic attack (in ...
Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...
Acid-catalyzed hydrolysis of esters produces carboxylic acids that also catalyze the same reaction. Indeed, the observation of an accelerating hydrolysis of gamma valerolactone to gamma-hydroxyvaleric acid led to the introduction of the concept of autocatalysis in 1890. [4] The oxidation of hydrocarbons by air or oxygen is the basis of ...
Pig liver esterase (PLE) is a widely used enzyme for asymmetric ester hydrolysis. Although it was originally used for the desymmetrizing hydrolysis of glutarate esters, [3] PLE also hydrolyzes malonates, cyclic diesters, monoesters, and other substrates. Active site models have been advanced to explain the selectivity of PLE. [4]