Q2: Ranking Acidity a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly explain the ranking. Use Table 2.2 as reference. Ha Нь HC H-N Ha OHe b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is more acidic? Explain. (Hint: use resonance structures to help) Name the functional groups on atenolol. H H-N atenolol Ν H-N OH Н

Q2: Ranking Acidity a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly explain the ranking. Use Table 2.2 as reference. Ha Нь HC H-N Ha OHe b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is more acidic? Explain. (Hint: use resonance structures to help) Name the functional groups on atenolol. H H-N atenolol Ν H-N OH Н

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.33P: Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label...

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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.
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