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org/wiki/Esterification
Esterification
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Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor. This leads to their extensive use in the fragrance and flavor industry. Ester bonds are also found in many polymers. Esterification is a reversible reaction. Hydrolysisliterally "water splitting"involves adding water and a catalyst (commonly NaOH) to an ester to get the sodium salt of the carboxylic acid and alcohol. As a result of this reversibility, many esterification reactions are equilibrium reactions and therefore need to be driven to completion according to Le Chatelier's principle. Esterifications are among the simplest and most often performed organic transformations. The most common esterification processes involve nucleophilic acyl substitution where the carbonyl compound is used as an electrophile and is attacked by a nucleophilic alcohol. However, other processes are possible; esterification by alkylation reverses the roles of "classic" carbonyl chemistry: a carboxylate anion is used as a nucleophile that displaces a halide ion in an SN2 reaction.
Contents
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1 Fischer esterification 2 Reaction with acyl halides 3 Reaction with acid anhydrides 4 Alkylation of carboxylate salts 5 Other methods 6 See also
the equilibrium in the desired direction. In addition to being the catalyst for the reaction, the sulfuric acid also removes water to help shift the equilibrium towards forming more of the ester product. Alternatively, where the ester has a suitable boiling point, it may be distilled off, once again causing the equilibrium to favor the product. For example, esterification of acetic acid in excess ethanol (possibly as the solvent) in the presence of concentrated sulfuric acid as a catalyst results in an ester (ethyl acetate):
Transesterification, a reaction to transform one ester into a different ester. Hydrolysis, the cleavage of an ester with water back to a carboxylic acid and alcohol. acetylation acylation
Retrieved from "http://en.wikipedia.org/wiki/Esterification" Categories: Carbon-heteroatom bond forming reactions | Condensation reactions Hidden categories: Articles lacking sources from December 2009 | All articles lacking sources
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