Chapter 23, Problem 1STP

Interpretation Introduction

Interpretation: To predict the product of acid-catalyzed reaction hydrolysis of an ester.

Concept Introduction: Catalysis is added to increase the rate of a chemical reaction. In acid-catalyzed hydrolysis, a protic acid is used as a solvent to cleave the chemical bond through a nucleophilic substitution reaction by adding molecules like water.

Answer to Problem 1STP

Alcohols

Explanation of Solution

Acid-catalyzed hydrolysis of ester will take place through a unimolecular nucleophilic substitution reaction. The acid which acts as a catalyst in this reaction protonates the carbonyl carbon of the ester making it liable for the nucleophilic attack.

  

In the above reaction, the ester will undergo protonation and makes the carbonyl carbon more electrophilic making it liable for the attack of the nucleophile. The lone pair of electrons that are present on the oxygen atom of the water molecule will attack the electrophilic center and then result in the formation of an intermediate. This intermediate will undergo further reaction to produce carboxylic acid and alcohol.

Conclusion

This acid-catalyzed reaction is reversible. The catalyst used here is used to increase the rate of the chemical reaction and the lone pairs present in the oxygen of ester will also participate in the reaction. The product is formed by protonation and nucleophilic attack.