Problem: Complete the following two structures by adding appropriate numbers of lone pair electrons, H atoms, and formal charges to the atoms in the boxes. You must adjust your answers to indicate the predominant species at each indicated pH value. (You do not have to add anything such as H atoms to atoms not drawn in the boxes.) This problem is testing your understanding of the relationship of protonation state to pH to pKa values for certain functional groups we have discussed. Next, in the space provided, write the overall charge on each structure at the indicated pH. For your reference, here are the relevant pKa values:

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Complete the following two structures by adding appropriate numbers of lone pair electrons, H atoms, and formal charges to the atoms in the boxes. You must adjust your answers to indicate the predominant species at each indicated pH value. (You do not have to add anything such as H atoms to atoms not drawn in the boxes.) This problem is testing your understanding of the relationship of protonation state to pH to pKa values for certain functional groups we have discussed. Next, in the space provided, write the overall charge on each structure at the indicated pH. For your reference, here are the relevant pKa values: