Date of Award
Gary P. Lutz, Ph.D.
Statistically designed experiments were developed and executed in order to determine the effects of several variables on the regiochemistry of electrophilic aromatic substitution (EAS) reactions. One experiment employed the electrophilic aromatic bromination of phenol, and indicated that temperature and concentration had statistically insignificant effects on the product composition of the reaction , while the mole ratio of bromine to phenol and percent water content of the solvent had significant effects at the 95% confidence level (i.e. a=0.05). Another experiment investigated the Friedel-Craf ts acylation of three butylbenzene isomers, and showed that temperature and reaction time had insignificant influences on product composition, while solvent dielectric constant and substrate substitution pattern had a significant influence (a=0.05). Together these experiments suggest that chemometric methods may be useful in investigating even well understood reactions. The Friedel-Crafts acylation experiments also the initial stages in the development of a quantitative method for describing steric effects. Inaddition, a laboratory exercise was designed and incorporated into Longwood University' s Organic Chemistry Laboratory II course. The implementation of the exercise was evaluated and suggested that students are receptive to new teaching styles.
Mann, Jason Adam, "Statistically Designed Experiments in the Examination of Factors Influencing Regioselectivity in Electrophilic Aromatic Substitution Reactions" (2008). Theses, Dissertations & Honors Papers. 186.