Expanding the Scope of an Electrophilic Aromatic Substitution Discovery Experiment Including Hydride and Methyl Shifts

Autor/inn/en	Savakinas, Mallory V.; Frey, Olivia M.; Piro, Nicholas A.; Rhile, Ian J.; Hamann, Christian S.
Titel	Expanding the Scope of an Electrophilic Aromatic Substitution Discovery Experiment Including Hydride and Methyl Shifts
Quelle	In: Journal of Chemical Education, 98 (2021) 12, S.3999-4008 (10 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Zusatzinformation	ORCID (Piro, Nicholas A.) ORCID (Rhile, Ian J.) ORCID (Hamann, Christian S.)
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
DOI	10.1021/acs.jchemed.1c00558
Schlagwörter	Science Instruction; Spectroscopy; Science Experiments; Teaching Methods; Light; Problem Solving; Organic Chemistry + Suchen Sie Ihr Suchwort? Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht; Spektroskopie; Teaching method; Lehrmethode; Unterrichtsmethode; Licht; Problemlösen; Organische Chemie
Abstract	Friedel-Crafts alkylation reactions using a curated set of alcohols provide students with the opportunity to combine the study of electrophilic aromatic substitution with carbocation rearrangements. In this experiment students may be presented with up to nine alcohols that yield six products, all synthesized under identical reaction conditions. They distinguish their products using a range of instrumental methods including infrared, [superscript 1]H NMR, and [superscript 13]C NMR spectroscopies, and mass spectrometry. Additional characterization is provided by the determination of melting point/mixed-melting point and gas chromatographic retention time. Students work in teams to assign structures to their individual reaction products; providing nine starting materials ensures minimal duplicates in a given laboratory section. As students interpret their data, some discover that a carbocation rearrangement occurred, resulting in isolation of only one product despite starting from a pair of isomeric reagents. This laboratory provides students with the opportunity to engage in a range of laboratory and problem-solving skills, and thus is designed to be performed toward the end of a two-semester organic chemistry sequence. (As Provided).
Anmerkungen	Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2024/1/01