Candyland!Winter '11 SSG

Leading Question!

Queen Frostine wants to learn more about the "Synthesis of Esters from Acid-Sensitive Alcohols!"

Esterfication

Esterification reactions take place between a carboxylic acid and an alcohol. Esterification with a carboxylic acid and alcohol cannot take place in the presence of a base because bases can deprotonate the hydrogen from the carboxylic acid prior to the reaction forming a carboxylate anion. This would prevent the nucleophilic alcohol from attacking the carbonyl carbon. Instead, an acid/proton donor must be used to donate a proton to the carbonyl oxygen. This allows for the oxygen of the alcohol to attack the partially positively-charged carbon of the carbonyl group of the carboxylic acid. Once this occurs, the -OH group of the carboxylic acid leaves as a water molecule. The product that is formed is an ester.