Our base choice determines how much of the original acid is left in solution at equilibrium. This will have significant consequences during our discussion of the Aldol and Claisen reactions. For each of the reactions below determine which is the most acidic proton in the first molecule. Assign a pKa value to at least the most acidic proton. Draw the expected conjugate base and acid. Assign a pKa value to the conjugate acid then determine the approximate position of the equilibrium (towards the starting material, towards the product, or near the middle - for example there would be a significant amount of starting material and product at equilibrium). Then predict the product of the reaction of the conjugate base with the reagent over the next arrow. An example is provided below. Alcohol 16 Alcohol 16 HO st pKa = Most acidic HO 10 Phenol 38 Amine Albuterol pKa 10 stronger acid OH NaOCH HO HOCH₂ 16 pKa 16 weaker acid favored at equilibrium Difference in pKa values = 6 = 6 orders of magnitude difference therefore >99% of molecules look like product, very little neutal phenol and NaOCH, would be present in solution. OH HO 305x

Our base choice determines how much of the original acid is left in solution at equilibrium. This will have significant consequences during our discussion of the Aldol and Claisen reactions. For each of the reactions below determine which is the most acidic proton in the first molecule. Assign a pKa value to at least the most acidic proton. Draw the expected conjugate base and acid. Assign a pKa value to the conjugate acid then determine the approximate position of the equilibrium (towards the starting material, towards the product, or near the middle - for example there would be a significant amount of starting material and product at equilibrium). Then predict the product of the reaction of the conjugate base with the reagent over the next arrow. An example is provided below. Alcohol 16 Alcohol 16 HO st pKa = Most acidic HO 10 Phenol 38 Amine Albuterol pKa 10 stronger acid OH NaOCH HO HOCH₂ 16 pKa 16 weaker acid favored at equilibrium Difference in pKa values = 6 = 6 orders of magnitude difference therefore >99% of molecules look like product, very little neutal phenol and NaOCH, would be present in solution. OH HO 305x

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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