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Esterification of Ethanoic Acid Esterification of Ethanoyl Chloride
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Formation of an Ester from Ethanoic Acid
Above shows the equation for the formation of an ester from ethanoic acid and an alcohol, this reaction also requires an acid catalyst (normally H2SO4 or HCl). The purpose of the acid catalyst is to increase the polarity of the C=O bond so the carbon end becomes slightly more positive, making it easier for the alcohol to attack it, leading to the formation of the ester. During the formation of an ester from an acyl chloride, no acid catalyst is need as the Cl atom is a much better leaving group (see the section on esterification of acyl chloride).
This diagram shows the mechanism for the formation of an ester from a carboxylic acid, the role of the acid catalyst can be clearly seen. Note how the H+ comes from H3O+ not from H2SO4, the reasoning for this is simple - when an acid is added to water, the H+ will be taken on by water molecules, and SO42- ions will be left in solution, if you would like to know more about this I would recommend looking on the internet or in a text book for "acid in solution" |