Hydrolysis Functional Group Flashcards
What happens during the hydrolysis of an ester?
Water breaks the ester into a carboxylic acid and an alcohol, often catalyzed by acid or base.
Why can methylphenidate only be taken multiple times daily and not as a single large dose?
Methylphenidate’s methyl ester is prone to hydrolysis, producing inactive ritalinic acid, which affects its duration of action.
How can hydrolysis be beneficial in drugs like diphenoxylate?
Hydrolysis converts diphenoxylate to difenoxin, which is more active and effective as an antidiarrheal agent.
What problem does oral administration of salicylic acid pose?
It can cause gastric bleeding due to its phenolic hydroxyl group
How does aspirin use a prodrug strategy?
Aspirin masks the phenolic hydroxyl group of salicylic acid as an ester, which is later hydrolyzed in the body to release the active salicylic acid.
Why must aspirin be stored properly?
Moisture can cause unwanted hydrolysis, converting aspirin to salicylic acid, which reduces its effectiveness.
What are examples of complex carbonyl groups?
Carboxylic acids, esters, and amides, each with different reactivity and types of leaving groups.
What makes amide hydrolysis different from ester hydrolysis?
Amides are more stable and require harsher conditions (acid or base catalysis) for hydrolysis.
How does the stability of a drug influence its storage advice?
Knowledge of hydrolysis helps inform proper storage, such as keeping aspirin bottles tightly closed to prevent moisture damage.
