Alkyl Halides Lab Report

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Nikea McMullen Alcohols to Alkyl Halides, IR and NMR December 5, 2014 Introduction The conversion of an alcohol to an alkyl halide can proceed by either the SN1 or SN2 mechanism, depending on the structure of the starting material. In an SN1 reaction, the formation of a carbocation intermediate is the rate-determining step. As a result, carbocation stability is important. Tertiary carbocations are the most stable, due to hyperconjugation and the induction effect, which both help stabilize the charge of the cation (1). Secondary and tertiary carbocations are commonly observed by SN1 reactions. On the other hand, primary carbocations are the least stable and therefore, the least observed by SN1 reactions. This is because of how slow the reaction…show more content…
In SN2 reactions, the opposite is true. Halomethanes and primary halides are generally the most favored and have less steric hindrance; thus, these structures allow the nucleophile to reach the substituted carbon more easily. Tertiary halides are rarely observed by SN2 reactions because of too much steric hindrance from the alkyl groups. Polar aprotic solvents are favored over polar protic solvents so that the nucleophile is freer to react. In this particular SN2 mechanism with an alcohol, the halide anion will attack the R group while the H2O leaves. In order to determine the results of the reaction, spectroscopy can be used. Spectroscopy is a process that uses a spectrum to study the structure of a molecule. There are many different types spectroscopy that can be used, but for this lab, Infrared (IR), and Nuclear Magnetic Resonance (NMR). IR spectroscopy is based off the idea that when bonds absorb energy, they will vibrate. The bond is compared to a spring, and it can either be compressed or stretched. The bonds can either experience symmetrical stretching, asymmetrical stretching, in-plane bending, or out-of-plane bending. Since each bond vibrates differently, IR spectroscopy…show more content…
In order to maximize products, and optimize the results, properly setting up the simple distillation apparatus and making sure all the vapors had condensed and collected in the distillate would maximize product and optimize the results of the experiment. Carefully taking as much of the organic layers as possible from the separatory funnel will also maximize product and optimize the results. Work Cited Hill, R.K.; Barbaro, J. Experiments in Organic Chemistry, 3rd edition; Contempory Publishing Co. of Raleigh, Inc.: North Carolina, 2005. NMR: Introduction. University of California, Davis. http://chemwiki.ucdavis.edu/Physical_Chemistry/Spectroscopy/Magnetic_Resonance_Spectroscopies/Nuclear_Magnetic_Resonance/Nuclear_Magnetic_Resonance_II Brown, W.H.; Iverson, B.L.; Anslyn, E.V.; Foote C.S. Organic Chemistry, 7th edition; Cengage Learning: California, 2013. Nerz-Stormes, M. The Basics Nuclear Magnetic Resonance Spectroscopy. Bryn Mawr College. http://www.brynmawr.edu/chemistry/Chem/mnerzsto/The_Basics_Nuclear_Magnetic_Resonance%20_Spectroscopy_2.htm Characteristic IR Absorption Frequencies of Organic Functional Groups. http://www2.ups.edu/faculty/hanson/Spectroscopy/IR/IRfrequencies.html "Spectroscopy Types." News-Medical.net. Web. 4 Dec. 2014.
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