Carbocation Rearrangement in An Electrophilic Aromatic Substitution Discovery Laboratory

Autor/inn/en	Polito, Victoria; Hamann, Christian S.; Rhile, Ian J.
Titel	Carbocation Rearrangement in An Electrophilic Aromatic Substitution Discovery Laboratory
Quelle	In: Journal of Chemical Education, 87 (2010) 9, S.969-970 (2 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
DOI	10.1021/ed9000238
Schlagwörter	Organic Chemistry; Laboratory Experiments; Science Experiments; Spectroscopy; Science Instruction; College Science; Science Activities + Suchen Sie Ihr Suchwort? Organische Chemie; Laboratory work; Laborarbeit; Spektroskopie; Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht
Abstract	In this discovery laboratory, students performed electrophilic aromatic substitution reactions between 1,4-dimethoxybenzene and either 2-methyl-2-butanol or 3-methyl-2-butanol with sulfuric acid as a catalyst. The carbocation from 3-methyl-2-butanol undergoes a hydride shift, and hence, both reactions afford 1,4-bis(1,1-dimethylpropyl)-2,5-dimethoxybenzene in high yields. NMR spectroscopy, infrared spectroscopy, mass spectrometry, and the melting point all indicate identical products from both reactions. Students determine the product identity from the spectroscopy results. Melting point and gas chromatography confirm that the products are identical, promoting discussion of carbocation stability and the hydride shift mechanism. (Contains 2 notes and 1 figure.) (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	2017/4/10