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Nucleophilic Substitution Lab Report

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Conducting Results from Various Substitution Reactions that Contain Alcohol Sophia Gruszczyk, Riley Clark Department of Chemistry and Chemical Biology, IUPUI, 402 N. Blackford St., Indianapolis, IN 46202. segruszc@iu.edu The purpose of this experiment was to determine the structure of a specific product(s) from a given starting material. The reaction that was tested was that of substitution reactions, whether it was SN1 or SN2. Reaction 1 is an SN2 reaction because of the presence of a strong nucleophile and the solvent being polar aprotic. Reaction 3 favors SN1. Since the solvent is polar protic, there is a weak nucleophile, and there is a secondary substituent. For this reaction there were two products, the minor being 3-chloro-2,4-dimethylpentane and the major being 2-chloro-2,4-dimethylpentane. Chemical reactions help scientists organize and understand how substances transform periods. substitution reactions involve swapping one atom or group for another and can occur in two ways: SN1 and SN2. An SN1 reaction is a unimolecular nucleophilic substitution and is 1st order while an SN2 reaction …show more content…

Preparation of 1 required the alcohol starting material (3.50 g, 0.023 mol) and sodium bromide (2.88 g, 0.028 mol) to be added to 5 mL of 9M H2SO4 and heated very carefully, due to its high boiling point, under standard reflux conditions for 25 m. While under reflux, the reaction developed two layers; a top reddish layer and a bottom clear layer. Following reflux, the resulting reaction material was allowed to cool and liquid material was pipetted away from excess NaBr solid. Extraction of the collected material with 1 x 15 mL of water and 2 x 10 mL of 5% NaHCO3, followed by drying with sodium sulfate, gave the oil 1 (3.68 g, 0.017 mol, 75%). 1H NMR (CDCl3, 200 MHz) 7.6-7.0 (m, 4H), 3.51 (t, 2H), 2.62 (t, 2H), 2.34 (s, 3H), 2.12 (p, 2H). IR (cm-1) 3106, 3087, 2968, 1951, 1882, 1806, 1496, 1454, 1227, 1069, 758. GC (TCD) 3.57 m

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