The Importance Of Fischer Esterification

Fischer Esterification is a unique type of esterification first discovered by Emil Fischer and A Speier in 1895. Fischer Esterification is a mechanism of which an ester is formed as a product when a carboxylic acid is treated with an alcohol and an acid catalyst. Together with ester, water is also liberated on this reaction. The key bonds formed in this reaction is C-OR, of which the oxygen bonded to carbon is the oxygen from the alcohol, not the oxygen originally bonded to it from the starting carboxylic acid. The key bonds broken is C-OH, the oxygen from the carboxylic acid bonds with the hydrogens that will then form water. So, the reaction does not simply just break the H and the R but rather -OH and -OR. This reaction is an equilibrium reaction. Applying Le Chatelier’s principle, if alcohol is used as a solvent to carboxylic acid and have a small amount of water (product), then the reaction would favor the product. On the other hand, if the reaction is to go backwards, whereas the reaction would start from an ester going to a carboxylic acid, then the water would be used as a solvent. Common acid catalyst are sulfuric acid, tosylic acid, and Lewis acids such that of scandium(III) triflate. Tertiary alcohols are prone to elimination whereas phenols
Non-complicated acidic conditions can be utilized if acid-sensitive functional groups are not an issue; sulfuric acid can be used or even softer acids - for longer reaction tomes. There will be less environmental effect in terms of harmfulness and product wastes of the reagents used because these are straightforward. As per Wikipedia, alkyl halides are greenhouse gasses or ozone depletors, therefore will possibly poison to the atmosphere. Another point was made is that acid anhydrides are more reactive than ester because carboxylate anion is better leaving group than an alkoxide anion because the negative charge is more