Nucleophilic Substitution Lab Report

Nucleophilic Substitution: Preparation of 1-Bromobutane & Alkyl Halide Classification Tests
Reference: Experimental Organic Chemistry: A Miniscale and Microscale Approach 6th ed., by Gilbert and Martin, Chapter 10 and Chapter 14
Discussion:
The purpose of this experiment is to look deeper into the nucleophilic substitution bi-molecular conversion of a primary alcohol, 1-butanol, into a primary bromoalkane, 1-bromobutane, using hydrobromic acid from the reaction between sodium bromide and concentrated sulfuric acid. The strong acids allow for the protonation of the basic hydroxyl functional group, to convert it to a good leaving group for the substitution. The next part of the experiment, alkyl halide classification tests, will be used to determine the degree of substitution of the alkyl halide that was formed during the reaction. For this experiment specifically, this allows for the verification of the formation of a primary bromoalkane from the primary alcohol. The success of the experiment will be determined by a percent yield, analysis of the infrared spectroscopy reading, and the results of the alkyl

There were no problems with either test individually as determined by the precipitates that were formed within a reasonable amount of time. There is a discrepancy in the overall data since the product appeared to react much more quickly to the silver nitrate test results, which should favor an SN2 mechanism. There was a lack of control reactions that could have been done with the alkyl halide tests so there were no comparisons that could be made with the reactivities of each test individually. Overall, the results were somewhat expected because the sodium iodide test usually takes about three minutes to form sodium bromide from a primary alcohol, although the silver nitrate test results were inconclusive due to no