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2018 Bankrate, LLC All Rights Reserved. R can also be a hydrogen atom. The word ‘ester’ was coined in 1848 by a German chemist Leopold Gmelin, probably as a contraction of the German Essigäther, “acetic ether”. Ester names are derived from the parent alcohol and the parent acid, where the latter may be organic or inorganic. Esters derived from the simplest carboxylic acids are commonly named according to the more traditional, so-called “trivial names” e. IUPAC nomenclature methanoate, ethanoate, propanoate and butanoate.
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Cyclic esters are called lactones, regardless of whether they are derived from an organic or an inorganic acid. Esters can also be derived from an inorganic acid and an alcohol. So far an alcohol and inorganic acid are linked via oxygen atoms. C bonds has a low barrier. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.
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Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Esters are generally identified by gas chromatography, taking advantage of their volatility. This peak changes depending on the functional groups attached to the carbonyl. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor. H2O The equilibrium constant for such reactions is about 5 for typical esters, e.
The reaction is slow in the absence of a catalyst. Sulfuric acid is a typical catalyst for this reaction. Other drying agents such as molecular sieves are also effective. Removal of water by physical means such as distillation as a low-boiling azeotropes with toluene, in conjunction with a Dean-Stark apparatus. Reagents are known that drive the dehydration of mixtures of alcohols and carboxylic acids.
One example is the Steglich esterification, which is a method of forming esters under mild conditions. The method is popular in peptide synthesis, where the substrates are sensitive to harsh conditions like high heat. N2 Using this diazomethane, mixtures of carboxylic acids can be converted to their methyl esters in near quantitative yields, e. The method is useful in specialized organic synthetic operations but is considered too hazardous and expensive for large-scale applications. R This reaction is employed in the production of vinyl ester resin resins from acrylic acid. RCO2H The reactions are irreversible simplifying work-up. Since acyl chlorides and acid anhydrides also react with water, anhydrous conditions are preferred.
Although not widely employed for esterifications, salts of carboxylate anions can be alkylating agent with alkyl halides to give esters. OH Like the hydrolysation, transesterification is catalysed by acids and bases. The reaction is widely used for degrading triglycerides, e. Alkenes undergo “hydroesterification” in the presence of metal carbonyl catalysts. C2H5CO2R The carbonylation of methanol yields methyl formate, which is the main commercial source of formic acid. H2O Direct routes to this same ester are not possible because vinyl alcohol is unstable.
Carboxylic acids also add across alkynes to give the same products. Ozonolysis of alkenes using a work up in the presence of hydrochloric acid and various alcohols. Anodic oxidation of methyl ketones leading to methyl esters. Esters react with nucleophiles at the carbonyl carbon. H bonds adjacent to the carbonyl are weakly acidic but undergo deprotonation with strong bases. This process is the one that usually initiates condensation reactions. Esters undergo hydrolysis under acid and basic conditions.