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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]
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]
In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC(OR') 3. Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic acids and it is from these that the name 'ortho ester' is derived.
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 ...
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 ...
Krapcho decarboxylation is a chemical reaction used to manipulate certain organic esters. [1] This reaction applies to esters with a beta electron-withdrawing group (EWG). The reaction proceeds by nucleophilic dealkylation of the ester by the halide followed by decarboxylation, followed by hydrolysis of the resulting stabilized carbanion. [2]
In the case of esterification with acetic anhydrides the currently accepted mechanism involves three steps. First, DMAP and acetic anhydride react in a pre-equilibrium reaction to form an ion pair of acetate and the acetylpyridinium ion. In the second step the alcohol adds to the acetylpyridinium, and elimination of pyridine forms an ester ...
In biochemistry, an esterase is a class of enzyme that splits esters into an acid and an alcohol in a chemical reaction with water called hydrolysis (and as such, it is a type of hydrolase). A wide range of different esterases exist that differ in their substrate specificity, their protein structure, and their biological function.