CHEM 237 Lab Fall 2009 Objective The purpose of this experiment is to perform oxymercuration and demercuration of an alkene to prepare an alcohol. 5 Reagents: 1-hexene NaBH 4 3M NaOH 10 Tetrahydrofuran (THF) MgSO 4 Apparatus Round bottom flask 15 Drying tube TLC plate (SiO 2 ) Glass pipette and micropipette Graduate Cylinder Theory 20 25 Alkenes possess a C-C double bond that consists of a σ and a π-bond. The π bond is much reactive than the σ bond and can be broken to produce two sigma bonds. Electron rich and nucleophilic alkenes will react with many different electrophilic reagents. Oxymercuration –demercuration involves the addition of water into an alkene to produce an alcohol (Scheme 1). H 2 O Hg(OAC) 2 NaBH 4 H H R R H H R R OH HgOAc Demercuration H H R R Hg OAc H 2 O Scheme 1. Oxymercuration-demercuration reaction of alkene 1 2 H H R R OH H Makovnikov orientation : nucelophilic water attack more substituted carbon. 30
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