Pharmaceutical Sciences 3320 - Principles of Drug Action

Functional Groups and Acid Base Chemistry

Study Questions

Please provide the appropriate answer for the following questions. Make sure you do not view the solution to a given problem until you have attempted to answer it using your BRAIN!

1. Assign all chiral centers in the following molecules either R or S:

Click the compass: It will guide you to the correct solution.

2. Consider the acid-base reaction below:

Aspirin is a weak acid with a pKa of 3.5

a. Assuming the pH of gastric fluid is 1.5 and the pH of intestinal fluid is 5.5, what is the percent ionized in the stomach?
b. In the duodenum?
c. Which of the two sites is the most likely absorption site for aspirin?

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3. Identify the following compounds as being ACIDIC, BASIC, AMPHOTERIC (having both acidic and basic functional groups) or NEUTRAL. Circle the functional groups responsible for the identified acid/base property.

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4. The tertiary amine of morphine has a pKa of 8.4, and the phenolic group has a pKa of 9.4. Assuming no interaction between these two groups, what percentage of the drug would be present in plasma (pH = 7.4) in the following forms:

a. Amine ionized?
b. Phenolic group ionized?
c. Both groups on one molecule ionized?
d. Both groups on one molecule unionized?

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You have now completed the study questions. Give yourself a star!

(O.K. it's hokey, but I'm running out of fun stuff!)

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