Practice 1-1 - Be sure to draw out any and all by-products....

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Chemistry 436 Professor Paul J. Hergenrother University of Illinois, Urbana-Champaign Old Test # 1a - You must use pencil for the exam. - Illegible answers cannot be graded and will receive no credit. NAME:________________________________ 1 21 points 2 18 points 3 9 points 4 42 points 5 10 points total 100 points
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1. Predict the major product in the following transformations. Please show stereochemistry, where appropriate. If there is no reaction, simply write “No Reaction”: (3 points each) OH O OH acid O OH O Acid, molecular sieves MeOH as solvent OH H O O 1 equivalent of CH 3 CH 2 MgBr 1) 2) Aqueous workup O 1) 1 equivalent of NaH, room temp. 2) EtBr O H O 2 equivalents of EtOH catalytic acid molecular sieves PPh 3 1 equivalent of n-BuLi propanal O OOH O a) b) c) d) e) f) g) (this enantiomer only)
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2. Predict the products and draw out mechanisms for the following transformations.
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Unformatted text preview: Be sure to draw out any and all by-products. (6 points each) O NH 2 NH 2 NaOH heat a) O O acid, H 2 O b) CN strong acid H 2 O heat c) 3. Please draw 3 different ways to effect the following conversion, drawing mechanisms for each. (9 points) OH O OMe O 4. Please complete the following syntheses: (7 points each) OEt O OH OEt O OH O OH a) O OH O OH b) HO OH HO OH O c) OH O OH O d) O OH OMe OH O O e) f) OH OH 5. Charged molecules are typically not absorbed through the stomach, whereas uncharged molecules are readily absorbed. (10 points) a) If you assume the stomach has a pH of ~3.0, would you expect the molecule below to be absorbed or not absorbed? b) Draw the structure of a carboxylic acid that you think would be less well absorbed than this compound. O OH...
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Practice 1-1 - Be sure to draw out any and all by-products....

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