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MT1Key_Wi04 - NU Winter 2004 l 1(20 pts For a gives both...

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Unformatted text preview: NU, Winter 2004 l 1. (20 pts) For a, gives both the common name and the IUPAC name of the structure shown. For b-f, complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction. say ‘ (We I ~ . so. ' COMM: W CSoprVXQ 2X74». rt O . \/ 7/ idec: Z’MW LW M can 4% a) Céonpouazmwe, 1) Na, NH3 (liq), —780C 2) mCPBA 41"; — W b) “2.192% O Y O H I 4, :Azon: excess H l H ‘+ \n/KOH e excess / §// 3) H25 excess 0 4w: / ———» o o O 9’“ + HMH + HA'OH C) Br 1) KOH (200°C) 2) H30+ H ————-—-—-———-—-—~> 3) Lindlar's catalyst, H2 4) Hg(OAc)2, MeOH 5) NaBH4 m s: \ lil d) 9mm) {90 M) _ _L_*—.a 2x e) 3) QEOTWM—W’ OH 445 Q) (Ade at) (*1, NU, Winter 2004 2. (20 pts) Propose a curved arrow mechanism for the following reaction sequence, showing every proton—transfer steps. Assuming that the ring—opening of the bromonium ion does not have a significant participation of the carbocation resonance form (i.e., the nucleophile attack in a completely anti-fashion), please indicate all the proper stereochemistry in your mechanism. 1) Brz, H20 2) NaOH, EtOH MeO V \ 3) NaOMe 0H m 6" 4) H3O+ Work up NU. Winter 2004 3 3) (20 pts) Propose a curved arrow mechanism for the following reaction sequence, showing every proton—transfer steps. Hint: Beware of making something analogous to an enol too early in the mechanism. The ester hydrolysis should be the last process. H2804, H20 fl >—E'0Et OH + EtOH NU, Winter 2004 4 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, PC C, 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. OR?) 0:” :> WA 90: Lari; “0 our / / Wolfe C, ' LCLH W [A :cH +2t+c NU, Winter 2004 5. (20 pts) Suggest sequence 0 reactions for the synthesis of the follovving\$olecule\t‘rom propene as the only carbon—co taining sta ing materials. You may also use O3/MCZS, CPBA, NBS, tosyl _ chloride, pyridine, P C, 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 (that is reactions which involve alkyne) may help you simplify your strategy. NU, Winter 2004 6 6. (20 pts) Starting with 1-butyne as the only carbon-containing starting materials, propose a reaction sequence for the synthesis of the following molecule. You may also use O3/MeZS, mCPBA, NBS, _ tosyl chloride, pyridine, PCC, Swern’s reagent, and any inorganic reagents. ...
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