MT1_Wi03 - NU Winter 2003 1 1(30 pts Complete the following...

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NU, Winter 2003 1 1. (30 pts) 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) 1) ozone excess 2) Me 2 S excess 3) H 2 O excess 2 O H H H OH O O + 2 b) 1) mCPBA 2) EtOH, H 3 0 + 3) PCC c) 1) OsO 4 , H 2 O 2 2) LAH excess 3) HIO 4 d) Br 1) KOH, hi heat 2) H 3 O + , EtOH e) OEt f) OTs
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NU, Winter 2003 2 2. (15 pts) Fill in the structures of A , B , and C . Propose curved arrow mechanisms for the following reaction sequence (no need to draw out the structure of Sia). Show all the proton transfer steps. You can buy the structures of A for 3 pts each and those of B and/or C for 2 pts each. O 1) 1-propyne,NaH 2) H 3 O + work up A 1) Sia 2 BH 2) H 2 O 2 , NaOH 3) H 3 O + work up B + C
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NU, Winter 2003 3 3) (15 pts) Fill in the structures of D and E . Propose a curved arrow mechanism for the conversion of D to E . Show all the proton transfer steps. You can buy the structures of D and/or E for 3 pts each.
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