Bringing Green Organic Electrochemistry to Undergraduates: A Designed Comparison Organic Experiment of Bromination

Abstract

The demand for sustainable synthetic methods in modern industry has been increasing rapidly due to the requirements of environmental protection and energy conservation, which has brought organic electrochemical synthesis to the forefront nowadays. Here, a two-part laboratory experiment has been designed to train undergraduates in comprehending and learning related concepts and operations of organic electrochemistry. First, students are required to perform a traditional bromination reaction of bisphenol A (BPA). In the second part, students need to achieve bromination of BPA in electrochemical conditions. Since tetrabromobisphenol A (TBBPA) is the common product of the two methods above, students are able to assess sustainability from multiple dimensions via 12 principles of Green Chemistry, which provides an excellent opportunity for undergraduates to focus on variables and sensitivities in experimental operations.

The Application of Dibromohydantoin in Chemical Experiment Pedagogy

“…α-Bromoacetophenone and its derivatives serve as crucial intermediates in organic synthesis, finding extensive applications in the production of functional chemicals like pharmaceuticals and pesticides. − These compounds are primarily obtained through α-site bromination of acetophenone derivatives with various substituents. Presently, the Journal of Chemical Education has documented various bromination reactions encompassing aromatic rings, olefin, and benzyl groups. − However, there is a lack of teaching experiments reporting on the bromination reaction at the α-carbon of carbonyl compounds, primarily due to the absence of safe and environmentally friendly bromination reagents. Liquid bromine and N -bromosuccinimide (NBS) are commonly employed as brominating agents. , Liquid bromine exhibits certain drawbacks, including volatility, high toxicity, strong corrosiveness, and limited reaction selectivity.…”