Abstract:

The electrophilic addition reactions of alkenes and the elimination reactions of alkyl halides are two fundamental reactions that undergraduates should master in basic organic chemistry course, but are rarely included in the laboratory course. The disconnection between theory and practice leads to the poor understanding of the reaction mechanisms. To address this disconnection in organic chemistry instruction, we design an experiment containing an electrophilic addition reaction and an elimination reaction. In this experiment, we use isopulegol as the starting material to synthesize the expensive R-citronellal in a one-pot two-step manner at room temperature through an electrophilic addition and a Grob fragmentation (a special elimination). The experiment features low cost of reagents, simple operation, mild reaction conditions and comprehensive skill training, therefore, it is a qualified teaching experiment that could help students deepen their understanding of theoretical knowledge while polishing their organic laboratory techniques.

Key words: Lsopulegol, R-citronellal, Electrophilic addition, Grob fragmentation, One-pot method