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Journal Abstracts | Michigan Green Chemistry …
The implementation of the green, one-pot Wittig reaction into the sophomore organic chemistry laboratory was a profitable endeavor because the students were able to observe first-hand the “greening” of a seminal organic reaction and understand the benefit of reducing the amount of organic waste that is generated in the organic chemistry laboratory. In addition, the students were able to perform column chromatography under conditions that more closely resembled a research laboratory environment; the clear and colorless appearance of the crude reaction mixture necessitated that the students utilize TLC (which was previously added to their synthetic toolbox) in order to successfully locate and isolate the Wittig products from the collected fractions. The reaction was simple to execute, and the reaction conditions were amenable to variation in both the aldehyde component and the alkyl halide component ().
The implementation of green chemistry experiments in the sophomore organic teaching lab is essential in order to increase student awareness of issues that pertain to sustainability and reducing waste that impacts the environment. Aspects of green chemistry that draw attention to these important issues include, but are not limited to, the use of safer solvents, the development of energy efficient reactions, the use of less hazardous chemicals, and the prevention of waste. To demonstrate the ease of introducing green chemistry principles into the organic chemistry teaching lab a Wittig reaction was chosen to be “greened.” The green Wittig reaction described within this report was performed at ambient temperature and in an aqueous medium; in addition, the reaction was complete within one hour, and the transformation was accomplished in “one-pot.” Finally, students analyzed the Wittig products using 1H NMR spectroscopy to confirm structure and to determine the :ratio.
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Recently, Bergdahl and coworkers  reported an aqueous Wittig reaction that could be performed in the sophomore organic chemistry laboratory. The reaction was amenable to a variety of aldehydes, and the products were synthesized in poor to excellent yields. In addition, the reaction could be completed within 30 minutes. However, the conditions for this reaction did not adhere to the principles of green chemistry; the aqueous solution had to be refluxed to afford the desired products, the reaction was performed on a multi-gram scale that resulted in a copious amount of waste, and two equivalents of ethyl bromoacetate was required to access the products.
The Wittig reaction described within this report is an excellent example of how traditional organic chemistry experiments can be modified to ensure that green principles are being discussed and promoted within a traditionally non-green discipline. The reaction is performed in one-pot, which circumvents the need to pre-form the phosphonium salts or ylides in a separate reaction that requires the use of copious amounts of deleterious solvents; this report is an improvement upon the “green” Wittig reactions that have thus far been published in the literature. In addition, the reaction was performed in a saturated, aqueous solution of sodium bicarbonate, which is an environmentally benign and green solvent thus reducing the amount of organic waste that is generated within the organic chemistry laboratory. The analysis of the 1H NMR and IR spectra of the Wittig products is a great opportunity to improve the critical thinking and analytical skills of the students. In closing, the Wittig reaction described in this report was a great introduction to advanced synthetic transformations that reinforced techniques learned over the course of the two semesters of organic chemistry.
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