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1998
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December
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In the Laboratory
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Lab Experiment
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Reduction of 2,6-Dimethylcyclohexanone with Sodium Borohydride Revisited: A Correction on the Structural Assignments of the Products, and the Discovery of a Solvent Effect
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Bruce A. Hathaway
Southeast Missouri State University, Department of Chemistry, MS6400, One University Plaza, Cape Girardeau, MO 63701-4799
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December 1998
Vol. 75 No. 12
p. 1623
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| Abstract |
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In a previously published article in this Journal (Garner, C. M. J. Chem. Educ. 1993, 70, A310-A311), 2,6-dimethylcyclohexanone was reduced with sodium borohydride in methanol to form 2,6-dimethylcyclohexanol. Product assignment was done by GC, according to previous literature results (Wigfield, D. C.; Phelps, D. J. J. Am. Chem. Soc. 1974, 96, 543-549.). NMR analysis clearly showed the major component to be the cis-cis isomer rather than the trans-trans isomer, as claimed in the previous work.
Changing the solvent from methanol to ethanol produced a different ratio of cis-cis to trans-trans than was reported in the original work. Therefore, a short series of solvents was investigated to determine if there was a solvent effect. The results indicate that as the size and bulk of the solvent increase, the proportion of the trans alcohol product increases.
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| Supplement |
The experimental procedures, report format, and questions are available as a Microsoft Word document, which has been compressed into a sit (Macintosh) and a zip (Windows) file. There is also a pdf file of the handout and may be accessed using Acrobat Reader.
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| More Information |
Citation |
Hathaway, Bruce A. J. Chem. Educ. 1998 75 1623.
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Keywords |
Organic Chemistry; Stereochemistry; NMR Spectrometry; Laboratory Instruction
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History |
Created:
Last Updated: |
June 18, 1999
November 22, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1998
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December
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1623
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