New Perspectives in Science Education

Edition 13

Accepted Abstracts

Greening the Organic Chemistry Laboratory: Comparing Synthetic and Purification Techniques in Organic Process Development

Devin Latimer, University of Winnipeg (Canada)


The third annual ACS Green Chemistry Summer School participants noted that incorporation of a general knowledge of green chemistry should begin at the undergraduate level and continue through graduate course work. Further, it has been noted that, rather than developing new techniques, achieving greener chemistry in many cases will simply require a redirection of current techniques. In this study, an experiment is described for the undergraduate organic chemistry lab which compares microwave-induced organic reaction enhancement (MORE) to that of more traditional synthetic procedures. MORE and traditional reflux procedures for substituting thiocyanate, ethylamine and diethylamine nucleophiles for bromide in nucleophilic aromatic substitution reactions on 1-bromo-2,4-dinitrobenzene as well as characterization by 13C NMR and mass spectrometry are described. Oral presentations by the class (where MORE procedures are consistently observed to be quicker, easier, result in higher yields and “greener”) leads to a discussion of general synthetic methods and provides the impetus for students to research the microwave effect as well as the 12 principles of green chemistry. We are currently developing a series of process oriented guided inquiry learning (POGIL) experiments whereby organic compounds will be isolated from an unknown mixture by column chromatography as well as liquid-liquid extraction and then the environmental factor (E factor) and process mass intensity (PMI) metrics determined for each of the separation techniques. 

Keywords: Third-Year Undergraduate, Chemical Education, Laboratory Instruction, Organic Chemistry, Green Chemistry;


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