Resumen de Synthesis of a Bromohydrin:: An Experiment Demonstrating Markovnikov Addition
Diane J. Porter, Andrea T. Stewart, Carl T. Wigal
The fundamental principle of regiospecific electrophilic addition to alkenes is Markovnikov's rule. Despite the significance of this principle, the only reported experiment for the organic chemistry laboratory that demonstrates Markovnikov addition is oxymercuration, an experiment that has the unfavorable aspect of generating mercury metal. We have developed a microscale experiment based on the bromohydrin derived from 1-methylcyclohexene which alleviates the generation of noxious material yet demonstrates, unequivocally, the fundamental concepts of Markovnikov addition. Synthesis, purification, and product characterization using both instrumental methods and qualitative analysis are presented.
