Examination of Alkyl-Halide Formation as a Result of Substitution Reactions of Alcohol-Containing Organic Compounds

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.This experiment was performed to determine the structure of alkyl-halides formed as a result of substitution reactions, and whether the reaction used an SN1 or SN2 mechanism. The structure of the starting alcohol determined the mechanistic pathway of the substitution reaction. Reaction 1 involved the substitution of a primary alcohol which produced one primary alkyl-halide via SN2 reaction. Reactions 2 and 3 began with a secondary alcohol, forming two products as the result of direct substitution and/or a hydride shift, via SN1 reaction. Reaction 2 formed two secondary alkyl-halides, and Reaction 3 formed one secondary and one tertiary alkyl-halide. The overall premise of the various experiments chronicled in this article is the determination of the mechanistic pathways and products formed via substitution reactions. Substitution reactions occur when one atom or functional group replaces another. For the purposes of this experiment, there were two types of substitution reactions: SN1 or unimolecular nucleophilic substitution, 1st order and SN2 or bimolecular nucleophilic substitution, 2nd order. 1 Substitution reactions, whether they are an SN1 or SN2 reaction, must contain molecules known as nucleophiles and electrophiles. The electrophile is a component of the substrate, in this case the starting alcohol, also commonly known as the “leaving group.” Electrophiles are electron deficient, while nucleophiles are “electron donating.” The mechanism of a substitution reaction is as follows: in the presence of the nucleophile, the leaving group separates from the substrate allowing the nucleophile to form a new bond with the substrate in place of the recently departed electrophile. 2 The key difference between the SN1 and SN2 me... ... middle of paper ... ...lpentane. 1H NMR (CDCl3, 200 MHz) δ 2.1-1.8 (nonet, 1H), 1.7 (d, 6H), 1.6 (s, 6H), 0.95-0.90 (d, 2H). 3-chloro-2,4-dimethylpentane. 1H NMR (CDCl3, 200 MHz) δ 3.6-3.5 (t, 1H), 2.6-2.4(octet, 2H) 1.1-1.0 (d, 12H). IR (cm-1) 2962.42, 743.14, 708.01. GC (TCD) 4.2 m (100%). Acknowledgements. Special thanks go to the Department of Chemistry and Chemical Biology at IUPUI, Dr. Ryan E. Denton, Professor and Dan Preston, TA. References. 4 1. Denton, R.E.; Audu, C. “Investigating Substitution Reactions of Various Alcoholic Compounds.” Fake Journal of Organic Chemistry 2010, 77, 3452-3453. 2. Klein, David. Organic Chemistry. Hoboken: John Wiley & Sons, Inc., 2012. Print 3. Balasubramanian, Satish. ChemWiki. University of California, Davis, (n.d.). Web. 29 APR 2014. 4. The Purdue Online Writing Lab. The Writing Lab and OWL at Purdue University, 2008. Web. 29 Apr. 2014.

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