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Final_I - A Nomenclature(15 points.5 points each Please...

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Unformatted text preview: A. Nomenclature: (15 points, .5 points each) Please: provide an acceptabl'E-nameforEach jof'fh'e-zfoliewing compounds. Bagsure'ie note stereochemiStry wherersappmpriate. fu 99ch H3 3. /w« l E: B. .Reactionsr'TFotal :: 4.0 poin’tsi 8. points each- PIe-asei'provide the major productFin {hex-answer box for FIVE-go? the-reactions. Wtiie"'~omit" in the-box of ihereaction‘ you CHOOSE-16' Zorn'it. Be Su're yourd'raw‘mgs indicate ister'eochemis‘try- if applicable. Partiaf credit is awarded O'nlyi;whe‘n- intermediate products'are's‘hdwn below the reacticn. Br 1 ' 1. HN03M-§SO4 - 2. H2 {PT ' 3. MN '02 1 H6! ‘4. mom 0. + (kerag 1. Heat ’ I 2; -»CH3NH2 f‘NaBHECN . N'éiCN‘rf". T 7" ” Lax-1+ ~ 4 _/ .0 1,-NaOE1JEtQHwhea1 K 22-'(:I;.5P-‘I—__-.C(CH3-}2 o _ . ., + 1 . {macaw-NH}. H 2. CH_3-—-C~CHrmCHC'H3 3.11730”? 1.‘CHSOH/'H+ 6 '-‘ 2._'Na20r207 / HQSC‘4_ _ ' 3. NHg [heat 4. BYE /NaOH J’HQC} C. MechaniSm: 1.5 points Please providega clear mechanism:er the. reaction below. Use curvadarrow notation. totindicate "eiedtron flo’w.““-Sh‘ow all Jnliermedlates and all formal changes. If’therei‘ismore‘thanone resonance structure, you-muSi Show the "best" (1.9., lowesfi e_ns_ar_gy)..structu_re. :0 '0 O D N OE fE’LOH _ ‘ _ _ _. ta: . t2 ‘ MOSHE T _ D. Synthesis”: (-1 5' points) Synthesize the compound .‘beiow «using any of thefquowingrreagents;:enzene and alkane‘s, 1flak-amass. gikynes'or alcohols-of'fhree carbons-orgies; :any oxidizing or'reducin‘g sagents...‘an,y= peroxyac‘gds, and any Inorganic reagents. Please note: A Starting material-may‘not contain more than-one functaonal gmup! F O H=¢QH~I E7? “Ha U .E._.'Spectros;<:npy: 15 Points A compound with the formula C4H9NO' exhibits theilR, 11H and proton—dhgtoupicd 13C. shown an the following page. Pleasuidemify this-compound‘anci‘sdrawéthemructure inihebdx-providéd belcm'. " 51 Ejfl Pr-nton NM? 3..u' £55." ‘ J -. WEE! . o J ’ 5 '10:; an 40 . Cat-bun i3 NEH Bonus Question: 10 points B'eiow are the 1R, 1H‘NMR, and proton‘edecouplged 13C: NMR Spectra Uta-compound OF-UHKFIOWH formula._ The-sin'gletiat 1' .3 ppm in The 1H NMR spectrumisflgfisexch‘angeabie. Propose a .s'tructUre‘for This-compound. Only-answer's in‘t‘helbo‘x will be graded. ' ‘ I z ‘ i L"""" ip'fcggnl valucs :5 5 LT". 9,9 Cami-um: I? ISM]. ...
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