MT1_Wi02 - NU Winter 2002 2 1(30 pts Complete the following...

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NU, Winter 2002 2 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) NaNH 2 2) CH 3 CH 2 OTs 3) NaNH 2 4) 5) H 3 O + dilute O b) O c) 1) Excess O 3 2) Excess Me 2 S 3) Excess H 2 O H O H OH O O + + HO O d) O e) Br H O O H O H f) O OH
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NU, Winter 2002 3 2. (15 pts) Propose a curved arrow mechanism for the following mechanisms. Show all the proton transfer steps. H + Br 2 O Br H 2 O 3) (15 pts) Propose a curved arrow mechanism for the following mechanisms. Show all the proton transfer steps. Hint: This is the second half of the permanganate oxidative cleavage of alkyne whose mechanism was assigned as homework. R O O R’ KMnO 4 , KOH H 2 O, Heat R O O- + R’ O -O R O OH + R’ O HO H 3 O +
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NU, Winter 2002 4 4. (20 pts) From methane as the only carbon-containing starting materials, propose a synthesis of the following molecule. You may also use NBS, tosyl chloride, pyridine, PCC, and any inorganic
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