CHEM3332FINALSPRING2006

CHEM3332FINALSPRING2006 - a;—~ mature(15 points axeptable...

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Unformatted text preview: a - ;—~_ mature: (15 points) - axeptable IUPAC name for each of the foilowing compounds. Be sure to indicate the :hemistry where appropriate. \ a. u- __ —-.A C :‘a. = 40 points, 8 points each _ . he starting material, reagents or major product in the answer box. Be _sure your drawing eochemistry if applicable. Partial credit is awarded only when intermediate products in a eaction are shown below the reaction. 3? S? C—O—CO H3 CH3 1. H30+ 2. (COCl)2 —————-————> 3. NH3 4. Big lNaOH /H20 CH3 1. LiAlH4 2. H O __LC)_._______> ll 3. OHS—OH lNaBchN g1 1. SOCI2 or P003 or P205 O O H H , 2.CH3—C- Hg—C-OET lNaOEt / 2.\l N 3-K] ._* 5m: (15 points) ‘3 a :eear mechanism to explain the formation of the product. Use curved arrows to indicate "electron - enembeflg Show only one step at a time. Show all intermediates and all formal charges. - s- more than one resonance contributor may be drawn, be sure to draw the most stable :: ~1ributor. OO\/ O o O , O O H /\ /W\/\/\/K 1.Na Et/EtOH O OA‘ 2. H30“ 0 reels: 15 Points - as :e the molecule below using any of the following reagents: benzene, any alkanes, alkenes, or ; -: = or three carbons or less, any Inorganic reagents, any ox1dlzmg or reducmg agents, and any a :=',-'acids. [CH20H3 O — H C———- CH --- C \ / '(‘ln CBHZ éH3 \ FE“ ..-' f" a . l . CH3 \' " {\j‘.\ :.:J y“ Chic; K {yr-Cl [II/z \_ y. d ‘F {fi’ ’“lr ’ ff -- _ //— lift/Ll J ' i I O , II' ’1 i I" '| ‘ _ x t I J. L" L/ .7 _.—-—F' I, ll / "fi r /r \‘ I pp." . L v '_1_ .| r._“Ir 4 ql --' ' -- r \ . _ / 7 r't, n 7 \I' \ 'L _ 'l -’ C \ K" "r " / " kw": .' 7 :a-ctroscopy: 15 Points _; wound with the formula CgHmO exhibits the leH NMR and proton decoupled “C NMR spectra .-,. '/. TRWETTFS‘ECE L.___l A // 2882 “n below. Please identify this compound and draw the structure in the box provided A ll below. w+———— . ——l ’ 8 8 / 3% V r 5 .l a“ a :3 1 — a g E 6_ _ was 3536 39m 2588 2530 1509 1 '- 1 WHERE 5 l—‘ i H l ' * l—J lH ll—l 9» i e 7 5 a 2 PPHLFI 51.9 m .07 integral values ET} 10.5 I Proton NMR 10 .34 I i :9 \ 31% In :5 w .1 1 :afocnlliNMR' lo Ex in {/Oil i» ‘- _ A \r_ 7 [l ‘_ Li 1 ' Flt ( '"_ ...
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CHEM3332FINALSPRING2006 - a;—~ mature(15 points axeptable...

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