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Unformatted text preview: Jae Shin 11/17/10 Experiment 10: Nucleophilic Substitution Reactions of Alkyl Halides Discussion For this lab experiment, we performed a series of chemical reactions of 11 different substrates in two separate solvents and analyzed the physical/chemical changes of the solution. In part I, we tested and observed the substrates in 18% solution of sodium iodide in acetone. 1-bromopentane in solution proceeded via SN2; CH 3 (CH 2 ) 4 Br NaBr+ CH 3 (CH 2 ) 4 I. The substrate was a primary halide and the iodine ion was a good nucleophile. 1- choloropentane did not react immediately at room temperature because chlorine is a bad leaving group with lower selectivity. However, once the solution was heated to 50 degrees Celsius, the reaction proceeded via SN2 as we observed the precipitate form. High temperature resulted in more molecular collisions to overcome the high transition state. Also, the physical property of the molecule allowed us to predict the reaction as SN2 and not SN1 because carbo-cations cannot be formed at primary carbons. CH 3 (CH 2 ) 4 Cl NaCL+ CH 3 (CH 2 ) 4 I. 2-bromopentane reacted via SN2 due to the presence of a good nucleophile and a good leaving group; the precipitate formed immediately. (CH 3 ) 2 (CH 2 ) 2 CHBr (CH 3 ) 2 (CH 2 ) 2 CHI +NaBr. 3-bromopentane proceeded via SN2; the reaction rate increased as CHI +NaBr....
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