The Study of Elimination Reactions Using Gas Chromatography采用气相色谱法消除反应的的研究.docVIP

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The Study of Elimination Reactions Using Gas Chromatography采用气相色谱法消除反应的的研究.doc

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The Study of Elimination Reactions Using Gas Chromatography采用气相色谱法消除反应的的研究

Chem 3125 Experiment #2 – The Study of Elimination Reactions Using Gas Chromatography. The Study of Elimination Reactions Using Gas Chromatography, Devin Latimer, J. Chem Ed, Vol 80, p. 1183, 2003 Introduction Elimination and substitution reactions (E1,E2, SN1, SN2) are among the most fundamental organic reactions. While each of these reaction types is relatively simple in mechanism, the 2 competing pathways complicate matters. In this experiment, you will investigate the effects of structural features of the alkyl halide and the base/nucleophile used on the outcome of the reaction. You will work in groups of 4-8 with each person completing a reaction between one of three alkyl halides and one of two bases, and the product distribution of each reaction will be analyzed by gas chromatography (GC). The GC data will be compiled by each student and then shared with the group. The effect of different bases/nucleophiles and primary versus secondary alkyl bromides gives a range of results that demonstrate the effects of substrate and nucleophiles on product distribution. Reactions Required Chemicals Reagent Molarity/MW Amount 1-bromopentane 151.04 10 drops, ~ 0.5 mL 2-bromopentane 151.04 10 drops, ~ 0.5 mL 2-bromo-2-methylbutane 151.04 10 drops, ~ 0.5 mL Na Methoxide 1.5 M 1.2 mL Na Ethoxide 1.5 M 1.2 mL K t-Butoxide 1.5 M 1.2 mL MTBE 10 mL Saturated NH4Cl Not relevant 2*10 mL Student Procedure You will be assigned a brominated alkane and a base for your particular elimination/substitution reaction. Note: the sodium methoxide, sodium ethoxide and potassium tert-butoxide salts will decompose on prolonged exposure to moisture in the air and so should be kept closed to the atmosphere as much as possible. In order to minimize contamination with water the condenser and RB flask should be dried in the oven for 20 minutes prior to setup. To minimize water contamination, setup your apparatus after drying before adding chemicals. In a 50 mL RB flask set up