A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides: Permanent Magnet [to the thirteenth power]C NMR in the First-Semester Organic Chemistry Lab

Autor/inn/en	Kjonaas, Richard A.; Tucker, Ryand J. F.
Titel	A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides: Permanent Magnet [to the thirteenth power]C NMR in the First-Semester Organic Chemistry Lab
Quelle	In: Journal of Chemical Education, 85 (2008) 1, S.100-101 (2 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
Schlagwörter	Organic Chemistry; College Science; Laboratory Experiments; Introductory Courses; Undergraduate Students; Structural Analysis (Science) + Suchen Sie Ihr Suchwort? Organische Chemie; Laboratory work; Laborarbeit; Einführungskurs; Strukturanalyse
Abstract	The use of permanent magnet [to the thirteenth power]C NMR in large-section first-semester organic chemistry lab courses is limited by the availability of experiments that not only hinge on first-semester lecture topics, but which also produce at least 0.5 mL of neat liquid sample. This article reports a discovery-based experiment that meets both of these criteria. Students convert three alcohols to alkyl halides under acidic conditions and record the [to the thirteenth power]C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, they conclude that (i) with 1-propanol there is no carbocation rearrangement, (ii) with 2-pentanol there is a considerable degree of secondary-to-secondary carbocation rearrangement, and (iii) with 2,4-dimethyl-3-pentanol all of the alkyl halide formed is the result of a secondary-to-tertiary carbocation rearrangement. (Contains 1 table.) (As Provided).
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Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2017/4/10