Besides, during reflux, the reactant and production will evaporate and condensed back to liquid and run down back to the reactant flask. During this process, some volatile organic reactant such as alcohol and carboxylic acid or the products like ester might evaporate or escape into the atmosphere result in the low yield of ester.
In addition, during transfer of liquid, for example, transferring the liquid from a round-bottom flask to a separating funnel or transferring the organic layer from separating funnel back to …show more content…
Based on Le Chatelier's principle, increase the concentration of either carboxylic acid or alcohol can increase the yield of ester. Doubling either carboxylic acid or alcohol, the theoretical yield will increase to 85%, while when either one of the carboxylic acid or alcohol is tripled, the theoretical yield goes through 90%. Therefore, a ratio of 1:3 of alcohol: carboxylic acid should be used in ester synthesis. The reason why using a ratio of 1:3 of alcohol: carboxylic acid instead of using a ratio of 3:1 of alcohol: carboxylic acid because it is easier to remove excess carboxylic acid than excess alcohol as excess carboxylic acid will react with sodium carbonate during isolation