Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Which of the following esters will undergo alkaline hydrolysis most rapidly?
Correct answer
1
Step-by-step solution
Alkaline hydrolysis of an ester involves the nucleophilic attack of a hydroxide ion ( OH^- ) on the carbonyl carbon. The rate of this reaction is directly proportional to the magnitude of the positive charge (electrophilicity) on the carbonyl carbon. Electron-withdrawing groups (EWG) increase the positive charge on the carbonyl carbon, thereby facilitating the nucleophilic attack and increasing the rate of hydrolysis. Conversely, electron-donating groups (EDG) decrease the positive charge, slowing down the reaction