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Quiz 3 - 4 or P P O OMe S N 2 style attach occurs from...

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CHEM 236 Spring 2011 Quiz 3 8:00 am Name Score: /20 1. (5pts) Describe mechanistically why two different epoxide opening products are obtained when treated with base or acid in the presence of methanol. vs. 2. (6pts) Provide a short synthesis of 2 of the 3 following molecules from the starting materials provided. (6pts) (Mechanisms are not necessary, please draw any intermediate compounds). CROSS OUT the one you don’t want graded. If there is nothing crossed out, I will grade the first two, regardless of which look completed. (±) (±) O OH OMe O MeO OH NaOMe MeOH dil. H 2 SO 4 MeOH OMe OH Me from m -CPBA O NaOMe MeoH P Br from OH Mg(0) MgBr O 1. 2. H+ n -BuLi Li CuCN Cu 2 O 1. 2. H+ P P or CH 3 OH H 3 C O CH 3 OH H 3 C O CH 3 O from 1. O 3 2. SMe 2 1. OsO 4 2. HIO
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Unformatted text preview: 4 or P P O OMe S N 2 style attach occurs from least sterically hindered side. S N 1 like OH O H + O H Stabilzed tertiary carbocation MeOH-H + OH MeO Determined by Sterics Determined by catrbocation stability 3. (8pts) Provide starting materials or products for the following transformations on the line provided. In the box, indicate whether this transformation is an oxidation (yes=oxidation, no=not and oxidation). 4. (1pt) If methanol has a pKa of 15 and phenol has a pKa of 10, which is more acidic? Phenol. pKa= - log(Ka) OH S Cl O O N Br PBr 3 CrO 3 O O O O H Cl oxidation? a. b. c. d. OH Cl yes no or SO 2 Ph OH no O yes...
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