Three inquiry activities for undergraduate organic chemistry laboratory work are described. The first involves the reduction of acetophenone with separation of stereoisomers by gas chromatography using a chiralcolumn. Students discover that a racemic mixture is obtained, supporting the known mechanism. IR and NMR spectroscopy are used to study the completeness of the reduction. In the second investigation, involving the Friedel–Crafts reaction of benzene and ethyl iodide, gas chromatography/mass spectrometry are used to identify various products. The rearrangement of one product under reaction conditions can be deduced by students. The third activity is the carbocation rearrangement of an SN1 reaction of a secondary alcohol. Students use 1H NMR to investigate the rearrangement and determine the extent of the rearrangement
Schreck et al. (Tue,) studied this question.