MT1_Wi07 - NU, Winter 2007 MT1 Chem 210-2 1 1. (20 pts) For...

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NU, Winter 2007 MT1 Chem 210-2 1 1. (20 pts) For a, gives the IUPAC name of the structure shown, be mindful of the stereochemical designation. 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) S b) CH 3 O c) 1) NaH 2) ethylene oxide 3) TBDMS-Cl 4) Sia 2 BH 5) H 2 O 2 , NaOH 6) MeLi 7) Swern’s reagent 8) NBu 4 F, H 2 O OH O d) 1) excess HgSO 4 and H 2 SO 4 2) Excess NaBH 4 3) H 3 O + work up 4) H 2 SO 4 conc., heat 2 Two possible products e) 1) excess HgSO 4 and H 2 SO 4 2) 2 MeLi 3) H 3 O + work up 4) H 2 SO 4 conc., heat 2 One product only
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NU, Winter 2007 MT1 Chem 210-2 2 2. (20 pts) As mentioned in class, the trimethylsilyl (TMS) protecting group is easily removed in aqueous acid and bases. Consider the protected alcohol below: O SiMe 3 a) Propose a full mechanism for the deprotection of its TMS group in aqueous acid.
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MT1_Wi07 - NU, Winter 2007 MT1 Chem 210-2 1 1. (20 pts) For...

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