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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.3. Arrange the following in order of decreasing basicity (strongest 1") CH,Li A B strongest ONa H₂NNa C CH₂SO,K D E weakest -ONa
- 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 ОНIn which of solvents A-E will CH;NH, be the weakest base? Explain. HO. CI4 A D E2. Arrange the following in order of decreasing acidity (strongest 1"). COH CH,SO,H O,N- -он HCI он C D E strongest weakest 3. Arrange the following in order of decreasing basicity (strongest 1") -ONa O,N- Nal Na Cl,CCO,Na A B D >_>_>_: strongest weakest
- Rank 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. Rank the following compounds in order of increasing acidity, putting the least acidic first. COOH CI I IFircle the compound with the most acidic hydrogen atom? SOH OH SMO CH || ||| 0716 NH₂ NH₂ IVRank the bold-faced hydrogens for the following compounds from most acidic to least acidic. Explain why?4. 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 "NH₂xSEE MORE QUESTIONS