2. For the following: a. Draw the Lewis structure for each anion. b. Rank the anions from most stable to least stable. c. Give a brief rationale for your ranking. d. Label the anions as "strongest base" and "weakest base" e. Draw the conjugate acid of each anion and label them as "strongest acid" and "weakest acid". f. Label each conjugate acid as "lowest pKa" and "highest pKa". i. F, I-, Br ii. H3C, HO, H₂N- iii. CH3CH2O, CH3CF2O, CH3CHFO iv. H3C-C=C I - C-H H-C=C -H H3C-CH2

For the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.

The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.

Use Table 13-2 to order the following from the strongest to the weakest acid. HClO2,H2O,NH4+,HClO4