51A-Guan-Disc2

51A-Guan-Disc2 - One of these nitrogens is more basic than...

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Discussion #2 Chem 51A 1. For the following reactions, identify each conjugate acid/base pair, and indicate which side the equilibrium favors. a. b. 2. Consider the following molecule having three labeled protons, H a , H b , and H c . Rank these protons in order of increasing acidity . Explain why based on orbital hybridizations. 3. Show the expected products from the following reactions. a. b. AlCl 3 + O 4. The following compound can become protonated on any of the three nitrogen atoms.
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Unformatted text preview: One of these nitrogens is more basic than the others, however. (a) Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms. (b) Determine which nitrogen atom is the most basic. OH O + NH 3 O O + NH 4 pKa = 4.8 pKa = 9.2 Li + -CH 3 + N H CH 4 + N pKa = 23 pKa = 48 BF 3 + O H H H 3 C H N C NH NH 2 5. Draw the possible resonance forms to show the delocalization of charges in the following ions. CH 2 NH O...
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51A-Guan-Disc2 - One of these nitrogens is more basic than...

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