.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 determines the mechanistic path of the substitution reaction. Reaction 1 involved the substitution of a primary alcohol producing a primary alkyl halide via the SN2 reaction. Reactions 2 and 3 started with a secondary alcohol, forming two products as a result of direct substitution and/or a hydride shift, via the SN1 reaction. Reaction 2 formed two secondary alkyl halides, while reaction 3 formed one secondary and one tertiary alkyl halide. The general premise of the various experiments described 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. 1Substitution reactions, whether SN1 or SN2, 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 donors.” 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 disappeared electrophile. 2The key difference between SN1 and SN2 is 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%). Acknowledgments. Special thanks to the IUPUI Department of Chemistry and Chemical Biology, Dr. Ryan E. Denton, Professor, and Dan Preston, TA.References. 41. Denton, R.E.; Audu, C. “Investigating Substitution Reactions of Various Alcohol Compounds.” False Journal of Organic Chemistry 2010, 77, 3452-3453.2. Klein, David. Organic Chemistry. Hoboken: John Wiley & Sons, Inc., 2012. Print3. Balasubramanian, Satish. ChemWiki. University of California, Davis, (n.d.). Network. 29 APRIL 2014.4. The Purdue Online Writing Workshop. The Writing Lab and OWL at Purdue University, 2008. Web. April 29. 2014.