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Unformatted text preview: Chem 3580 - Spring 2009 Problem Set #2 solutions Answer (3) correceted 1. Retrosynthesis Br coupling (Stille, Suzuki, or Gilman) Proposed forward synthesis Br B(OH)2 Pd(PPh3)4 NaOH NBS Peroxide Retrosynthesis H O H OH MgBr + O Forward synthesis Br Mg THF (solvent) MgBr O H OH MnO 2 , ! (Chem 358) H O or PCC (Chem 357) (Chem 357) (Chem 357) Retrosynthesis OH Heck Br Hydration slow but ok Cl AlCl 3 NBS, peroxide Br OH t-BuOK H 2 O H 2 SO 4 (cat) 2. Cl O Cl O SnCl 4 C O ClSnCl 4 + SnCl 4 + O C O O H O H O H O O O O O B...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell.
- Spring '09