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- 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.2A. Rank the following compounds with increasing acidity: (1 = least acidic; 3 = most acidic) Me Me Mo Me (c) Se H. (d) H. .H H.1. Which of the following compounds is most acidic? a. I b. Il с. ||| d. IV e. V I ОН II ОН Br III ОН Br Br IV ОН V F ОН
- 3. Arrange the following compounds in terms of their basicity (Strongest base first, weakest base last). CH;NHNA CH;ONa CH;OH HCO,NaRank the bold-faced hydrogens for the following compounds from most acidic to least acidic. H I O A. II > IV> ||| >V>I OB. II > IV> V> ||| > I OC. IV>II> I > V > III O D.V> III > IV> || > | OE. IV>II> ||| > V > I II CI CO₂H CKH Н III W n IV CO₂H2. Identify the most acidic H. Draw the conjugate base and Explain Thoroughly. HO N OH
- 2. Rank the following compounds in order of increasing acidity, putting the least acidic first. COOH CI I IWhich is the stronger acid, I or II (see below)? ** H₂N-CH₂ VS. H₂N-CH=CH₂ 11 Note: H₂N- protons are the most acidic H's in each molecule Select one: OA. II OB. Both are equally strong. O C. I5. Rank the highlighted protons from most acidic to least acidic. А. Ha ÓH most acidic least acidic OHd на Hb most acidic least acidic B.Label each molecule according to increasing acidity with 1 as the weakest and 4 as the strongest based on their structure. Explain.4. Label the three oxygens in compounds A, B, and C in order of Lewis basicity, with 1 being the most basic and 3 being the least. Explain your choice for the most basic one. B C H H H H F3C4. Rank the following compounds in decreasing (strongest to weakest) order of basicity. NH₂ O₂N || NH₂ NH₂ B. II > III >> IV E. III >II>I>IV 11 ||| A. I> ||| > || > IV D. IV > III >II>I 5. Predict the product for the following reaction. CN H₂/Ni NH₂ NH₂ A. IB. II C. III D. IV E. I and II IV NH₂ C. IV> | > | > IV CN IV "NH₂SEE MORE QUESTIONS