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Syn and Anti Isomer Preference in Oximes: An Undergraduate Organic Chemistry Experiment

  • Laboratories and Demonstrations
  • Published:
The Chemical Educator

Abstract

An experiment is described that links a nucleophilic carbonyl addition reaction to a study of structure–activity relationships. Students prepare a series of oximes (from readily available ketones and aldehydes) and, with the use of NMR, define the ratio of syn and anti isomers formed in the reaction. From these data, a quantitative assessment of the steric hindrance of hydrogen, methyl, ethyl, isopropyl, and t–butyl can be obtained.

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Authors and Affiliations

  1. Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849-1150

    Michael D. Mosher & Scott Meisenbach

Authors
  1. Michael D. Mosher
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  2. Scott Meisenbach
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Correspondence to Michael D. Mosher.

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Mosher, M.D., Meisenbach, S. Syn and Anti Isomer Preference in Oximes: An Undergraduate Organic Chemistry Experiment. Chem. Educator 7, 356–358 (2002). https://doi.org/10.1007/s00897020623a

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  • DOI: https://doi.org/10.1007/s00897020623a

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