Dichloromethane Lab Report

In this lab, the objective was to examine the effect of an SN2 reaction using a phase transfer catalyst in dichloromethane. We isolated the product of the phase transfer reaction by using liquid chromatography and then prepared TLC plates to see which of the five vials collected contained the isolated product and an IR spectrum was then obtained. The reaction in this lab was an example of an SN2 reaction. SN2 is a nucleophilic substitution reaction where one bond is broken and one bond is formed in one step. For example, a lone pair from the oxygen in naphtholate anion attacks the carbon that is bonded to bromine from an allyl bromide molecule. This creates a partial C-O bond and a partial broken C-Br bond, then the C-O bond fully bonds

The first visible peak was an sp3 C-H stretch at 3058.54 cm-1. The next peak was a C=C stretch at 1600.05 cm-1 and at 1628.97 cm-1. There was also a peak of an sp3 C-H bend at a range going from 1363.15 cm-1 to 1469.71 cm -1. The next peak was a C-O stretch at 1215. 40 cm-1. At the fingerprint region, there was an intense peak at 734. 51 cm-1, which could be the C-CL stretch found in dichloromethane, which means the product might not have been pure. This lab was successful to an extent because we were able to obtain the product, 2-naphthyl ether, but it was not pure since the IR spectrum showed traces of dichloromethane. Also the percent yield of the product was over 100%. Some sources of error in this experiment were that since the product in vial 3 had solidified, we had added a drop of dichloromethane to the vial, resulting in the C-Cl peak of the IR spectrum. Another error was that since the percent yield was over 100, there was an error in obtaining the mass of the vials because the same balance was not used. Also, the addition of the dichloromethane could have added to the mass and when calculating the percent yield, the mass of the dichloromethane was