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ERIC Number: EJ824927
Record Type: Journal
Publication Date: 2008-Jan
Pages: 2
Abstractor: As Provided
Reference Count: 6
ISSN: ISSN-0021-9584
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
Kjonaas, Richard A.; Tucker, Ryand J. F.
Journal of Chemical Education, v85 n1 p100-101 Jan 2008
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.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A