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MT1_Wi05 - NU Winter 2005 MT1 Chem 210-2 1 1(20 pts For a...

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NU, Winter 2005 MT1 Chem 210-2 1 1. (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 stereochemistry when relevant. If there is no reaction, say so. a) O Br b) 1) Na, NH 3 (liq), -78 o C 2) H 3 O wk up 3) mCPBA 4) NaOEt 4) EtI c) 1) Cl 2 , h ν 2) KO t Bu, heat 3) mCPBA 4) TsOH, MeOH 5) NaH 6) EtI OEt OMe d) Br Br e) O Br
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NU, Winter 2005 MT1 Chem 210-2 2 2. (20 pts) Propose a curved arrow mechanism for the following reaction sequence, showing every proton–transfer steps. H 2 O, H 2 SO 4 conc O OH
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NU, Winter 2005 MT1 Chem 210-2 3 3) (20 pts) Explain the following observations using the appropriate curved arrow mechanisms, showing every proton–transfer steps. OH HBr, H 2 SO 4 catalyst Br OH HBr, H 2 SO 4 catalyst Br
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NU, Winter 2005 MT1 Chem 210-2 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.
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