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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > January  >
In the Laboratory
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Permanent Magnet 13C NMR in the First-Semester Organic Chemistry Lab
Richard A. Kjonaas and Ryand J. F. Tucker
Department of Chemistry, Indiana State University, Terre Haute, IN 47809
Cover
January 2008
Vol. 85 No. 1
p. 100
Abstract
The use of permanent magnet 13C 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 13C 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.
Supplement
The student procedure, instructor notes, and spectra of the products are available.
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Citation
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
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Keywords
Alcohols; Carbocations; Gas Chromatography; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; NMR Spectroscopy; Nucleophilic Substitution; Organic Chemistry; Second-Year Undergraduate
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History
Created:
Last Updated:
12/4/2007
12/12/2007
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