Session S41a (Tuesday, 9:30am, Wartik 110)

P393: Inquiry-driven approach to Grignard chemistry in the lab

Sara Hein, Robert Kopitzke (Winona State University, USA)

Grignard reactions have long been part of the organic chemistry laboratory curriculum.  Dependable success rates, yields, and learning outcomes support its inclusion.  The transformation of bromobenzene to a Grignard, followed by benzophenone addition, achieves triphenylmethanol with little difficulty.  However, for students who are well-studied in its mechanism, carrying out a Grignard reaction may lead to an unspectacular response from them as they become simply cooks in the kitchen.

At Winona State University, we have employed a dihalogenated benzene for Grignard reagent formation that requires discernment of carbanion location. This reagent produces an alcohol that has unique NMR spectroscopic properties, characteristic of the presence of the additional halogen. The solid that is produced is easily recrystallized and elucidated using NMR spectroscopy. NMR spectral interpretation incorporates detailed integration and coupling that demands thorough understanding of NMR theory, adding another thought-provoking analysis to the experiment.


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