Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Isotopic Labeling with Sodium Borodeuteride in the Introductory Organic Chemistry Laboratory

A microscale isotopic labeling experiment is described for the introductory organic chemistry laboratory course wherein half of the students use sodium borohydride (NaBH4) and the other half use sodium borodeuteride (NaBD4) to reduce acetophenone to 1-phenylethanol and then compare spectral data. The cost is reasonable, and the experiment is well-suited to serve as a first experience with 1H NMR spectroscopy, infrared spectroscopy, and/or mass spectrometry. No special apparatus are required for the reaction. The entire experiment, including an extensive prelab lecture and acquisition of 1H NMR data, is completed in a 3 h period. The experiment can stand alone, but lends itself to cross-course collaboration between the organic and physical chemistry laboratories. The succeeding companion article describes the measurement of a kinetic isotope effect using the product from this experiment. The physical chemistry students report their experimental results back to the organic class.