Organic Chemistry Lab Outline

Christian Quintos

January 29, 2014

Locker #105, 108, & 111

Nucleophilic Substitution reactions of Alkyl Halides: All Sections from Lab Manual

References:

Fessenden, Ralph J., Joan S. Fessden, and Patty Feist. Organic Laboratory Techniques. 3rd ed. N.p.: Brooks Cole, 2001. Pg 163-178. Print

Jones, Martha. Laboratory Manual for Chemistry 212. N.p.: Department of Chemistry, Union County College, 1998. Pg 9- 16. Print

“Material Safety Data Sheet (MSDS) List.” Material Safety Data Sheet (MSDS) List. Science Lap, n.d. Web. 19 Sept. 2012 .

Experimental Objective:

The objective of these experiments is to find out how the variables such as the nature of nucleophiles, leaving groups, solvent and temperatures affect the rates of nucleophilic substitution reactions. These variables will be tested in three different sections with the effect of substrate structure on SN2 Reactivity, effect of substrate structure on SN1 Reactivity, and effect of solvent on reaction rate.

Experimental Theory:

SN2 reactions work by having a nucleophile attack from the opposing side of the carbon atom in order to have a pentavalent carbon atom and knock out the halogen on the other side. Some key components of the reaction are the types of solvents used and the how good Nucleophile is for the reaction. In this experiment the solvent of Acetone is being used because it is non-polar and does not promote ionization of the alkyl halide which increases the rate for the SN2 reaction. The Nucleophile for this reaction is (I-) which is a great nucleophile because it is polarizable. It also has a particularly large atom size which makes it have nucleophilicity, which in turn allows the reaction to happen at a quicker pace.

SN1 reactions are done by separating the halide from the alkyl group to form a carbocation and from there bonding the nucleophile with the carbocation. The key components here are the exact opposite of that of a SN2 reaction, for a SN1 reaction you would not need a...