Hydration硼氢化反应_new_new要点解析.docxVIP

Title：Hydration of alkenes by hydroboration-oxidation：preparation of octan-1-ol from 1-octene 、 1. Introduction/Background： Since 1937, American chemist Herbert Charles Brown had engaged in organic boron chemistry and completed the first paper(carbonyl compounds reduced by diborane) under the guidance of Professor Schlesinger of the University of Chicago. After that , Brown not only has made great achievements in theory but also invented dozens of reducing agents. Hydroboration-oxidation reaction is also found during the period. Brown was award the 1979 Nobel Prize in Chemistry. Brief Description of the Reaction. Reduction reactions between borane and unsaturated bonds belong to electrophilic hydride transfer mechanism. Borane can be made by sodium boron hydride and boron trifluoride. Diborane is dimer of borane, toxic gases, typically dissolved in tetrahydrofuran to use. In ether like tetrahydrofuran, there are the following equilibrium: In this experiment:, BMS was used. Borane is electrophilic hydride transfer reducing agent. It firstly attack electron-rich center. It is easy to reduce carboxyl group and can react with a double bond. 2. Objectives： To obtain certain knowledge about the mechanisms of Hydroboration-oxidation and Direct Hydration To learn how to identify simple artefacts 3. Experimental Data Reagents: M(Octene) = 25 mmol, Mw(Octene) = 8 x 12 + 16 x 1 = 96+16=112 g/mol m(Octene) = 25 mmol x 112 g/mol = 2.8g BMS: M(BMS) = (1/3 x 25) x 1.1 = 8.33 x 1.1 = 9.16 mmol BMS=H3B SMe = 75.9 g/mol m(BMS) = 9.16 mmol x 75.9 g/mol= 0.695 g V(BMS) = m(BMS) ÷ density= 0.695 g ÷ 0.801 g/ml = 0.867 ml M = (trimethylamine –N-oxide dihydrate) = 111.14 g/mol m（trim）= 25 mmol x 111.14 g/mol = 2.7785 g M(octene)MW(octene)m(Octene)M(BMS)m(BMS)V(BMS)M(trim)m(trim)25 mmol112 g/mol2.8 g9.16 mmol0.695 g0.867 ml111.14 g/mol2.7785 g final product: the weight of round bottom flask = 62.22 g the weight of all = 64.31 g the product = 64.31g – 62.22 g=2.09 g