Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Acid-catalyzed hydrolysis of esters is a reversible reaction. Which of the following statements is true regarding the base-promoted hydrolysis of esters?
Options
- AIt is irreversible because the carboxylate ion is resonance stabilized.
- BIt is a reversible reaction.
- CIt is irreversible because salts of carboxylic acids have high melting points.
- DIt is irreversible because salts of carboxylic acids are insoluble.
Correct answer
A. It is irreversible because the carboxylate ion is resonance stabilized.
Step-by-step solution
Base-promoted hydrolysis of esters, also known as saponification, involves the nucleophilic attack of a hydroxide ion on the carbonyl carbon of the ester, leading to the formation of a carboxylic acid and an alkoxide ion. The alkoxide ion, being a strong base, rapidly abstracts a proton from the carboxylic acid to form an alcohol and a carboxylate ion. The resulting carboxylate ion is highly resonance stabilized, distributing the negative charge equally over the two oxygen atoms. This resonance stabilization makes