The Low pKa of Methyl Acetate: Exploring the Unique Properties of the Ester Functional Group
The ester functional group is a common component of organic molecules, and understanding its properties is essential for organic chemistry. One of these properties is the acidity of an ester, which is typically lower than that of an alkane due to the presence of the carbonyl group. This is illustrated by methyl acetate, which has a pKa of 25, much lower than the expected pKa of 50 for a normal C-H bond (Hofmann, 2020). To understand why methyl acetate has such a low pKa, it is important to look at the three C-H bonds present in the ester. The pKa of methyl acetate is so low because one of the C-H bonds is a hydrogen attached to the carbonyl carbon, which is more acidic than a normal C-H bond. This is due to the resonance stabilization of the intermediate enolate anion, which has a more negative charge on the oxygen, allowing it to better accept a proton (Hofmann, 2020). Additionally, the other two C-H bonds are both allylic, meaning they are connected to a double bond, which makes them slightly… Cont…
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