Imagine you are developing a new over-the-counter pain medication. This compound

Question

Imagine you are developing a new over-the-counter pain medication. This compound contains a carboxylic acid functional group (pKa of 2.1) and an amine functional group (pKa of 9.0). In order to be absorbed into the bloodstream it must pass through the membrane lining the stomach or the small intestine. Electrically neutral molecules can pass through a membrane more easily than can charged molecules. Would you expect more of your new compound to be absorbed in the stomach, where the pH of gastric juice is about 1, or in the small intestine, where the pH is about 6? Explain your answer.

Explanation / Answer

For carboxyl: pKa<pH, so charge = 0.
For amine: pKa>pH so charge = 0.

Electrically neutral molecules can pass through a membrane more easily than can charged molecules

so This compound contains no charge so it can pass through the membrane.

Related Questions

Navigate

• Browse (All)
• Browse I
• Subjects

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.