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Unformatted text preview: Sophie Scheidlinger Nucleophilic Substitution Reactions of Alkyl Halides April 23, 2008 Purpose: To test the reactivity of 11 different alkyl halides with sodium iodide and ethanolic silver nitrate. Discussion: Bromopentane reacted in an SN2 reaction with NaI in acetone to form Iodopentane and NaBr. The mechanism reacted via SN2 because the strong nucleophile attacked the primary carbon adjacent to the good leaving group. Bromopentane also seemed to react in an SN1 reaction with ethanolic silver nitrate to form ethoxy pentane and AgBr and nitric acid, contrary to the prediction. There was some kind of human error that gave a false positive, possibly residue in the reaction tube or reactants mixing. Chloropentane did not react with either NaI (as expected) in acetone or ethanolic silver nitrate (contrary to predictions made). Chlorine is not a strong leaving group and it was a primary halide, so it would not react via SN1. 2-bromopentane reacted in an SN2 reaction with NaI in acetone to form 2-iodopentane and NaBr as expected. 2-bromopentane also reacted in an SN1 reaction to form 2-ethoxypentane and AgBr and nitric acid as expected. 2-bromopentane is a reaction to form 2-ethoxypentane and AgBr and nitric acid as expected....
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