Promblem Set #03 - O O O O OH OMe O HO NMe 2 N Me...

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Chemistry 436 Professor Paul J. Hergenrother Spring 2009 University of Illinois, Urbana-Champaign Problem set #3 Due in class at 8 AM on Friday, February 13 Turn answers in on a separate sheet of paper. For additional problems (not to be turned in), please see textbook Chapter 18 Problems 47-51 1) Predict the products and draw out the mechanisms for the following reactions. O LDA -78 o C H O O NaH room temp Br then H 2 O workup then H 2 O workup O O Et 3 Si-Cl Et 3 Si-Cl NaH room temp LDA -78 o C a) b) c) d)
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2) Synthesize the following: O From starting materials containing 5 or less carbons Cl OCH 3 OCH 3 O O O From starting materials containing 7 carbons or less a) b) c) d) 3) O HO OH OH O O O O O OH OMe O HO NMe 2 O HO OH OH
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Unformatted text preview: O O O O OH OMe O HO NMe 2 N Me erythromycin A Zithromax TM Shown above are structures of two antibiotics, erythromycin A, and Zithromax. Because erythromycin A breaks down in the acidic environment of the stomach, patients on erythromycin must take 1000 mg a day for 14 days; Zithromax is stable in the stomach, and thus patients need only take 300 mg a day for 7 days. Looking at the two structures, and remembering what you know about the reactivity of ketones, please draw the structure of the erythromycin A breakdown product. Why doesnt Zithromax breakdown in an analogous fashion?...
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Promblem Set #03 - O O O O OH OMe O HO NMe 2 N Me...

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