Which Molecule Would Experience the Slowest Hydrolysis Rate in an Aqueous NaOH Solution-

Which would be hydrolyzed most slowly with aqueous NaOH?

Hydrolysis is a chemical reaction that involves the breaking of a chemical bond by the addition of water. In the context of organic chemistry, hydrolysis often refers to the breakdown of ester, amide, or ether bonds. When these bonds are hydrolyzed in the presence of aqueous NaOH, the reaction rate can vary significantly depending on the specific compound. In this article, we will explore the factors that influence the rate of hydrolysis and identify which compound would be hydrolyzed most slowly with aqueous NaOH.

Factors influencing the rate of hydrolysis

The rate of hydrolysis of a compound with aqueous NaOH is influenced by several factors, including:

1. The nature of the bond: Ester, amide, and ether bonds have different strengths, with amide bonds being the strongest and ether bonds being the weakest. Generally, the stronger the bond, the slower the hydrolysis rate.
2. The structure of the compound: The presence of electron-withdrawing or electron-donating groups can affect the rate of hydrolysis. Electron-withdrawing groups can stabilize the negative charge on the intermediate, making the hydrolysis reaction more favorable.
3. The solvent: The choice of solvent can significantly impact the rate of hydrolysis. Aqueous NaOH is a polar solvent that can stabilize the intermediate and facilitate the hydrolysis reaction.
4. Temperature: Increasing the temperature generally increases the rate of hydrolysis, as it provides more energy for the reaction to occur.

Identifying the compound with the slowest hydrolysis rate

Considering the factors mentioned above, we can analyze the hydrolysis rates of various compounds with aqueous NaOH. Let’s take a look at three examples:

1. Ethyl acetate (ester): Ethyl acetate has a relatively strong ester bond, and the presence of the electron-withdrawing acetyl group stabilizes the intermediate. As a result, its hydrolysis rate is moderate.
2. Acetamide (amide): Acetamide has a strong amide bond, which is more difficult to break compared to ester bonds. Additionally, the electron-withdrawing acetyl group stabilizes the intermediate. Therefore, acetamide is expected to have a slower hydrolysis rate than ethyl acetate.
3. Diethyl ether (ether): Diethyl ether has a weak ether bond and lacks electron-withdrawing or electron-donating groups. Consequently, its hydrolysis rate is expected to be the fastest among the three compounds.

Based on this analysis, acetamide would be hydrolyzed most slowly with aqueous NaOH due to its strong amide bond and the stabilizing effect of the electron-withdrawing acetyl group.