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Organic Chemistry Course Development in a Forensic Science Program: Use of FT-NMR

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Ronald Callahan

Chemistry Department, New York University, New York, NY 10003

Lawrence Kobilinsky and Robert Rothchild

John Jay College, New York, NY 10019

J. Chem. Educ., 1999, 76 (10), p 1332

DOI: 10.1021/ed076p1332

Publication Date (Web): October 1, 1999

Abstract

The acquisition of a modern, multinuclear, medium-field (7 tesla) FT-NMR, with partial support from NSF-ILI, has made possible the introduction of a major special project for second-semester organic chemistry laboratory, within a forensic science program. The eight-week special project focuses on microscale syntheses of Diels-Alder adducts of phencyclone. Students synthesize a wide range of different N-substituted maleimides for use as dienophiles. The corresponding phencyclone adducts permit studies of: a) unusual hindered rotations of unsubsituted bridgehead phenyls, b) striking examples of magnetic anisotropic effects, and c) modern one- and two-dimensional NMR methods for structural characterization. Use of fluorine-containing dienophiles provides a basis for examining NMR spectra of three different NMR-active nuclei: proton, carbon-13, and fluorine-19. Variable-temperature NMR is also applicable to these compounds. Molecular modeling software has been introduced in the organic laboratory course for students to examine the geometry of these adducts, precursors, and simplified model compounds, and to evaluate geometric parameters in structures that are optimized by semi-empirical and ab initio calculations.

References are included with the article and can be accessed via its PDF file.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

NSF Highlights

Keywords (Subject):

Forensic Chemistry

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- Instrumental Proficiency Program for Undergraduates
  Duane E. Weisshaar , Gary W. Earl , Milton P. Hanson , Arlen E. Viste , R. Roy Kintner and Jetty L. Duffy-Matzner
  Journal of Chemical Education2005 82 (6), 898
  The instrument proficiency program was developed to complement coverage in the traditional curriculum by providing students with additional opportunities to gain in-depth experience with instrumentation and to make better use of departmental instruments ...
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