Sas-exam3practice - treatment with sodium amide in liquid...

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CHEM 239B Spring, 2006 EXAM #3 Name . Prof. Sasaki 150 points TOTAL Good Luck! Note: Only answers in the box will be graded. _______________________________________________________________________ 1. (35) (a) Draw the Fisher projection of the following carbohydrates. OHC OH H OH H OH HO H HO H OHC OH HO H H OH H OH HO H D-Galactose D-Mannose (b) Draw the Haworth projection for α -D-2-Deoxymannopyranose (b) Draw the most stable chair conformation of Methyl β -D-galactopyranoside.
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CHEM 239B page 2 Name . 2. (35) (a) Outline a reasonable synthesis of 4-nitrophenyl phenyl ether, starting from benzene as a sole carbon source. You may use any reagents that you wish. (b) 2-Bromo-1,3-dimethylbenzene is inert to nucleophilic aromatic substitution on
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Unformatted text preview: treatment with sodium amide in liquid ammonia. It is recovered unchanged even after extended contact with the reagent. Briefly explain why. CHEM 239B page 3 Name . 3. (40) (a) Draw a reasonable mechanism for the following reaction. O OH H H OH OH H H OH H COOH OH H O O H H OH OH H H OH H COOH -D-glucuronic acid b) Draw a stepwise mechanism for the following reaction. O Cl Cl Cl heat Cl Cl O O K 2 CO 3 OH Cl Cl Cl Cl CHEM 239B page 4 Name . 4. (40) Predict the major product(s) for each of the following reactions. If more than one product is expected, please put all of them in the box. (a) OH Cl Cl Cl + C 6 H 5 N N Cl (b) HN H 3 C O OCH 2 CH=CH-CH 3 heat (c) O H 3 C O O AlCl 3 (d) D D Cl NaNH 2 liq. NH 3 (e) OH OH Cl Cl K 2 Cr 2 O 7 H 2 SO 4...
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This test prep was uploaded on 04/15/2008 for the course CHEM 239 taught by Professor Sasaki during the Spring '06 term at University of Washington.

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Sas-exam3practice - treatment with sodium amide in liquid...

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