Q1_Wi07 - use of PCl 3 to prepare MeCl from methanol? In a...

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NU, Winter 2007, Quiz 1, Chem 210-2 2 1. (20 pts) For a, gives the IUPAC names of the structure shown. For b-e, complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry that the reaction may require. a. O Br b. OH 1) TsCl, py 2) excess NaI, acetone 3) Li[CuMe 2 ] c. OH 1) conc. H 2 SO 4 , heat 2) mCPBA 3) NaOMe 4) MeI d. O 1) H 2 O, H 3 O + 2) Na 3) ethylene oxide 4) H 3 O + OH e 1) heat, NaNH 2 2) MeC(O)H 3) Conc. H 2 SO 4
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NU, Winter 2007, Quiz 1, Chem 210-2 3 2. (12 pts) Propose a reasonable mechanism to account for the following reaction, which gives good yield of the (MeO)PCl 2 product. PCl 3 + MeOH + NEt 3 (MeO)PCl 2 + [HNEt 3 ]Cl What is the main difference between the above reaction and what we discussed in class regarding the
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Unformatted text preview: use of PCl 3 to prepare MeCl from methanol? In a few words, explain the key mechanistic difference that accounts for these two different pathways. You may use a diagram to illustrate your argument but remember to be brief. Wordiness can hurt you. NU, Winter 2007, Quiz 1, Chem 210-2 4 3. (18 pts). Propose a synthesis of the following compound from methane as the only carbon-containing starting material. You may use any necessary inorganic reagents, m CPBA, any alcohol protecting reagent, and any sulfur-containing reagent. Hint: If you dont know how to start from methane, start from a known 2-C starting materials that could be made from methane O O...
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Q1_Wi07 - use of PCl 3 to prepare MeCl from methanol? In a...

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