Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 24, Problem 12PP

Practice Problem 24.12

Show all steps in the synthesis of GVA using the tert-butyloxycarbonyl (Boc) group as a protecting group.

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Use solubility rules to provide balance molecular equation, total, and net ionic equation
Br HO ? HO ✓ OH
Use the literature Ka value of the acetic acid, and the data below to answer these questions. Note: You will not use the experimental titration graphs to answer the questions that follow.  Group #1:   Buffer pH = 4.35 Group #2: Buffer pH = 4.70 Group #3: Buffer pH = 5.00 Group #4: Buffer pH = 5.30 Use the Henderson-Hasselbalch equation, the buffer pH provided and the literature pKa value of acetic acid to perform the following: a) calculate the ratios of [acetate]/[acetic acid] for each of the 4 groups buffer solutions above. b) using the calculated ratios, which group solution will provide the best optimal buffer (Hint: what [acetate]/[acetic acid] ratio value is expected for an optimal buffer?) c) explain your choice
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