test_final_spring_06

test_final_spring_06 - Provide a clear mechanism to explain...

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Final Exam Name (PRINT) . Last, First Chemistry 3332 Signature May 3, 2006 ID# Please circle class time. TOTAL ACS Exam: # correct = Page # . Score 1. 15 pts. 2. 24 pts. 3. 16 pts. 4. 15 pts. 5. 15 pts. 6. 15 pts. Dr. Bean’s 10:00 AM Dr. Bean’s 1:00 PM
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A. Nomenclature: (15 points) Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. 1. N CH 2 O O OH 2. CH 3 O H CH 3 N 3. O N
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B. Reactions : Total = 40 points, 8 points each Please provide the starting material, reagents or major product in the answer box. Be sure your drawing indicates stereochemistry if applicable. Partial credit is awarded only when intermediate products in a multi-step reaction are shown below the reaction. 1. 2. (COCl) 2 3. NH 3 1. H 3 O + 4. Br 2 /NaOH/H 2 O C O C CH 3 CH 3 O O 2. NH 2 CN C CH 2 CH 3 O 3. 3. 2. H 2 O 1. LiAlH 4 C O CH 3 H /NaBH 3 CN N CH 3 CH 2 CH 3
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4. 2. 1. SOCl 2 or POCl 3 or P 2 O 5 3. H 3 O + / 180 °C C O NH 2 C O CH 3 CH 2 C O OEt /NaOEt 5. 2. 3. 1. Br 2 /CH 3 CO 2 H O N OCH 3 4. P CH 2 3
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C. Mechanisms : (15 points)
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Unformatted text preview: Provide a clear mechanism to explain the formation of the product. Use curved arrows to indicate electron flow. Remember to show only one step at a time. Show all intermediates and all formal charges. When more than one resonance contributor may be drawn, be sure to draw the most stable contributor. 1. NaOEt / EtOH O O O O O O 2. H 3 O + O O O O O O D. Synthesis : 15 Points Synthesize the molecule below using any of the following reagents: benzene, any alkanes, alkenes, or alcohols of three carbons or less, any inorganic reagents, any oxidizing or reducing agents, and any peroxyacids. C CH 2 CH 3 CH 2 CH CH 3 C O O CH 3 E. Spectroscopy: 15 Points A compound with the formula C 9 H 10 O exhibits the IR, 1 H NMR and proton decoupled 13 C NMR spectra shown below. Please identify this compound and draw the structure in the box provided below....
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test_final_spring_06 - Provide a clear mechanism to explain...

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