MT1Key_Wi05 - NU Winter 2005 I l(20 pts For a gives both...

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Unformatted text preview: NU. Winter 2005 I l. (20 pts) For a. gives both the common name and the IUPAC name of the structure shown. For b-e, complete the following reactions, be careful to give all the major carbon—containing products, starting materials, or reagents. Clearly indicate the stereocZemistry when relevant. If there is no reaction. say 2 "Pu/aftJHrzg NOwBr Z ~ J'FMF‘aNafl (561% d 0K 3.— (Z'meyoar) SO. 1) Na, NH3 (qu), -78°c 2)H O kup «Va ‘ _ 3) mizpvéA _, nzc (up t M HLO (that; 5 Z —> Add: 4) NaOEt Ft b) 4) Etl 1)C|2,hv 2) Ko’Bu, heat OEt ’ 3 CPBA : /\ 4)mS , e ""OMe 440 L) 5) NaH c) 6) Etl l) KCtpm )5 ‘ \ £601 ‘Br 4'!” >_Br a) We M d) gt? Na? 4) Hem) (l m \ ‘) NaNm 2 A ’ "i" o» e? B _ A) Hy, L t Mr 6) S) Lr’tJDtmfis CHI) rim 0 (it) Exhale s) PLL — lryf -. A’LUHA'L Gem‘wrmm“ 2) “€33 340 Wme Hwa M I?" i" NU, Winter 2005 7 2. (20 pts) Propose a curved arrow mechanism for the following reaction sequence, showing every proton—transfer steps. DEW?“ (Dc kg M, M, )‘O M ;‘V~— MDQATTBH Ole-AH A1461 NE :‘u 1%ch Tg/ flz?d,;c;. 763:,“ GLLW a.» : Or. 49W. wah)wmpu @taatflt Mm (61,175”??er art/go / Q .6 +w W V“ M) (fin/tale ' I J P H ~§HZ } \ \i ’ QO‘ ‘ ‘0 .‘O \ /\ Q};\U/ ‘y L ‘ '7 I L Q.) “56“ /53 \‘T ‘ 1/ W >\\\Od 7 W1 Hi0 I? NIH 3"\Ql/Uil NU, Winter 2005 3 3) (20 pts) Explain the following observations using the appropriate curved arrow mechanisms. showing every proton—transfer steps. fl/ HBr. H2804 catalyst Br %/ HBr, H2804 catalyst /Tr\/ of w“ —e ‘ “‘06” f 8% g“ Pl MO“ l/ ,2 Q '-*‘ 9 /l\/ . 9ft) {[5 Kw,“ é? " [x /(+ OH. wag-04 (l G.) ,9 —_‘———) ’F —-—-9 67 /k]/ 2 get; /\[/ 3ft fill 3pc /\{ Kf \/ l N NU, Winter 2005 4. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from methane as the only carbon—containing starting materials. You may also use O3/Me28, mCPBA, NBS, tosyl chloride, pyridine, PCC, Swern’s reagent, and any inorganic reagents. Hint: If you do not know how to make acetylene from methane, start the synthesis from acetylene to get partial credits. 0, mm (54, 1/49er “a Lemma MCPRA- @938.» :2 Zr; 2% / l)wa __-: ~—~——-—-—9 g... 2’)ng if}; \LLNDt/m :/ WSW £0 M No 5119610 ’70 Wtw ma. 4 "l 00% NU. Winter 2 005 5. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from propene as the only carbon-containing starting materials. You may also use Og/MeZS, mCPBA, NBS, tosyl chloride, pyridine, PCC, Swern’s reagent, and any inorganic reagents. Hint: Remember to count the number of carbons and use the most appropriate building blocks that you can derive from propene. Hint: Although non—alkyne solutions do exist for this problem, using alkyne—type reactions (i.e., reactions. which involve alkyne) may help you simplify your strategy. A Q l o o l Z 1;; (O ‘ \ I ~—\ ,, / f L //‘\ 19 LL/‘Lu’ +u/ll\ O W a” L “L s w it) Mata. l1 op L 0L L) H.301: 9 M NWd‘q) ‘ w U, 2) “10+ FNMA {A NU. Wmter 2005 6 6. (20 pts) What are the potential problems for the following reaction sequences. Propose alternate modifications to arrive at the desire product from the starting materials on the right. If there aren’t any. say 50' / NUT Bkgc‘c Spout?» T5 95‘ 0%4Céwwle M +1 p/c 1) KOH 2) 0'6 O A \ 5m 3) H30+ wk up > : ) | l a) 4) Na20r207, H2804 (—— yoch 959% we Cede, @ MODtT-Tckn‘w ; O NaNH; OIL (Jul (m &u @ fits CKéEP/L 3’3 ) (D (a g 4.) swaps a? (WAVE u‘sr: C(l‘ldfa)9mgoj SW @ Ma:3) W2, 1) sOH cat,NaOM "‘ 965% In» W ‘ M90) “km t‘s m & 2W3 VOH kwm McchPme’ 4x129 mm, a) b) / 0M9 mm k? Mafl£ merco e. MODCFT‘Um‘mJ ‘- TsolJr )W 41% mm men @ coat :‘2 9‘1 ‘3 f“ wat max) / M‘LL WWW/W ma: Merlot 2227" 63 1 Pro ne, NaNHz, rt 2) H3O wk. up. /\/\j 0 c) wc‘u, W THE CBC 2/ P N~ NJH‘L. ) gflj g3 fimwicdv Wt 4) swam/5 MW) [rt 1) Dilute st04 #014 §v0Me / 2) NaOMe k Nor (wa EMUG-r VD {WEE THE them—Jr, 1 Pt 938136, Wm J Am is emu Mava mm M 6m” are; (D d) HZSOQ (no MGDl Git MIN ‘. :1 01» Egg %" W ...
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