test_final_spring_07 - A Nomenclature(15 points Give an...

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Unformatted text preview: A. Nomenclature: (15 points) Give an acceptable lUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. 1/\n/\/\’/\/OCH3 "'__—_. __"l.-.'.'..I=:_'.._."' ..._"-_ '.." ' h:- '.T".'.'T-—-—' 1*": l 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. H CO 0 1. HEAT 3 / 1. + CH3 2_ H+, NH2 \ 3. NaBH3CN ' 4. H20 0 N02 NH2 CHQCHS 1_ CH31(exceSS) 2. Ag2O/H2O/heat . 3. MCPBA NHCHecHs 4. CH30H/H+ .‘I"! r- rye—r.- I .‘ 1. NaNOQ/HCI ——+ 2. 1 . NaOEt/EtOH 2. H3O+ C. Mechanism: (‘15 points) 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. “a. Q 0 OH O OH “4..., __ E D. Synthesis: 15 Points Synthesize the molecule below using any of the following reagents: benzene, aniline,any alkanes, alkenes, or alcohols of three carbons or less, any inorganic reagents, any oxidizing or reducing agents, and any peroxyacids. E. Spectroscow: 15 Points A compound with the formula 011H1404 exhibits the [RH NMR and proton decoupled 130 NMR spectrashown below. Please identify this compound and draw the structure in the box provided below. NOTE: The peak at 5.65ppm is D20 exchangeable. L: a [a Q ‘ 15, . 3 w l l ‘1 l I i w E l l l ' “- as i J '- L‘: E. a 44m 3558 l em F 15818 I 1m Copyright © 1994 W 3H 2H 3H 3H 2H 1H i “W 7.0 5.3 5.5 5.4 5.2 5.0 5.3 M 4,0 3. 3,0 2_ M L mm Proton NHR 180 150 140 120 100 80 60 40 20 PPM 0 ...
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