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Summer 08 exam 3

Summer 08 exam 3 - NAME CHEMISTRY 221 1:5 EXAM 3 H SCORE Be...

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Unformatted text preview: NAME CHEMISTRY 221 1 :5 EXAM 3 H July 16, 2008 . . . . SCORE Be sure to read each questlon carefully. Thls test must be taken 1n pen. Tests taken 1n pencil will not be graded. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1 E 1. ( 10 pts) Provide the proper IUPAC names for the following compounds in the spaces provided: 2_ ' 2 3. '§ 14 2 (o Br 4. E 5. [/1 / ‘S ,/L 6. 7. Cl 8. 9. 10. 1 1. Bonus: Total: 2. (10 pts) Provide a complete, detailed and stepwise mechanism for the following reaction. In order to receive full credit on must show all electron movement and rovide all of the intermediates for this reaction: CH3 Br2 WI, —> CH30H20H OCHZCH3 Br 3. (10 pts) Write a series of steps to accomplish the following synthetic transformation. You must provide all appropriate reagents and intermediates for your synthetic pathway. No reaction mechanisms (arrows) are necessary to answer this question. 0 O Acetylene ZI> MH + “H 4. (4 pts) Assign the appropriate designation of either Re or Si to the top (above the plane of the page) and bottom (below the plane of the page) faces of the pro-chiral carbon in the following molecule. In addition, assign the designation of Pro—R or Pro-S to each of the indicated hydrogens in the same structure. Write the appropriate designations in the appropriate spaces provided: T_og Face: Bottom Face: 5. (6 pts) Identify the relationship between the following pairs of compounds as: enantiomers, diastereomers, or identical compounds. Write the each appropriate designation in the box provided: OH CH C! 9' )\/COZH COZH )\/CHO ' CHO H020 . HOZC OHC . OHC/\r Br OH OH Br CH3 CH20H HOH2C' H30' v - H300 COZH H020 OCH3 Ida/xiv‘w‘cJ CONPOUAC‘J‘, .3 6. (10 pts) Assign the appropriate R and S designations to each of the chirality centers found in the following compounds. You must clear] indicate our answer for each chiral center. Be careful and make sure to double check your work. (“3(3sz OCH3 HOZC 7. (4 pts) Draw the two enantiomeric forms of the following condensed formula. Be sure to use dashed and wedged lines to clearly indicate the proper spatial orientation of each group around the chiral carbon: “.‘HZ CH3CHZC(OH)CH3 8. (6 pts) Draw the structures for all of the possible product(s) of the following reactions: Br ] KOH / ‘sf Jr “\i ——> 1 v 4 CH30H20H l \ \/>(k H2804, H20 0 A"’/ x m \ OH THF, 50 C \/ . 9. (12 pts) Complete the following reaction schemes by adding the appropriate reagent(s) and/or product(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary: NaOH —> 2 equivalents Br CI2 _ —> 1 equivalent HBr —> 2 equivalents 10. (12 pts) Complete the following reaction schemes by adding the appropriate starting material(s), reagent(s) and/or product(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary: HIO4 H20 1.) 0304 \/\ ——> 2.) NaHSOa, H20 H30 KOH CHC|3 l 7 2 v 1.) 03 —> Br '5 g 2.) Zn, H30+ 11. (16 pts) Draw all of the products formed in the following reactions. Indicate whether the product, or product mixture, is optically active by writing either YES or NO in the box provided: Is this product/prod uct mixture optically active (yes or no)? Mo Sweat 3W sis r O E M 1. BH3, THF 2. H202. CH C i/k/ 1. Hg(0Ac)2 2 NaBH4 COZH \ r i: S O (raoemic mixture) [£flAnHDM3fl1 6r ;/\ I I i i w 1 {CME W‘IOH iv 2 w" Hm 0H BONUS: (4 pts) Problem 9.55 - Assign R and S stereochemistry to the chirality centers in the following Newman projections: CI H H CH 20 H3 H30 0 H H 3C H H 3C C H3 H H 10 ...
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