Problem 5.2 Order the compounds below from most acidic to least acidic. What factors influenced your analysis?

Problem 5.3 Order the compounds below from most basic to least basic. What factors influenced your analysis?

Problem 5.4 Each drug molecule below is shown in its neutral state along with its experimentally reported pK_a value. For each molecule, write the relevant acid/base equilibrium for the reported pK_a value.

Problem 5.5 Shown below is a model of the drug paliperidone (Invega^®) interacting with six amino acid side chains of a hypothetical target. The drug has a basic functional group with a BH⁺ pK_a of ~8.1. Redraw paliperidone in its dominant protonation state at pH 7.4, labeling the basic group with its pK_a value. Finally, draw the side chains of the six amino acids making appropriate intermolecular interactions with the specific regions of the palperidone structure indicated below. Be sure to draw the interacting amino acid side chains in their appropriate protonation states.

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