The Low pKa of Methyl Acetate: Exploring the Unique Properties of the Ester Functional Group

Methyl Acetate’s Low pKa: Examining the Unusual Properties of the Ester Functional group

Understanding the properties of an ester functional group, a component common to organic molecules is crucial for organic chemistry. The acidity of an ester is one such property. It is generally lower than the alkane because of the presence of the carbonyl. The example of methyl acetate is a good example of this. It has a pH of 25 which is lower than what would be expected for a C-H bond. (Hofmann 2020). The three C-H bond present in methyl ester are important for understanding why it has such low pKa. Because one C-H bond is hydrogen attached to the carbonylcarbon, which is less acidic than the normal C-H bond, methyl acetate’s pKa is low. The resonance stabilization in the intermediate enolate anon allows it to accept proton better (Hofmann 2020). The two C-H bond are also allylic. This means they can be connected to a double bond.