ERIC Number: EJ1062162
Record Type: Journal
Publication Date: 2015-Mar
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Use of [superscript 1]H, [superscript 13]C, and [superscript 19]F-NMR Spectroscopy and Computational Modeling to Explore Chemoselectivity in the Formation of a Grignard Reagent
Hein, Sara M.; Kopitzke, Robert W.; Nalli, Thomas W.; Esselman, Brian J.; Hill, Nicholas J.
Journal of Chemical Education, v92 n3 p548-552 Mar 2015
A discovery-based Grignard experiment for a second-year undergraduate organic chemistry course is described. The exclusive Grignard reagent formed by the reaction of 1-bromo-4-fluorobenzene (1) with Mg is 4-fluorophenylmagnesium bromide (2), which is treated with either benzophenone or CO[subscript 2] to produce the corresponding fluorinated alcohol (3) or benzoic acid (4), respectively. The use of a dihalogenated Grignard reagent requires students to discern its reactivity for synthesis. Students predict the chemoselectivity of Grignard reagent formation based on the C-X bond energies of 1 and investigate their predictions by analysis of [superscript 1]H, [superscript 13]C, and [superscript 19]F NMR, EI-MS, and IR data of 3 and 4. Empirical parameters and DFT calculations are used to predict the [superscript 1]H and [superscript 13]C NMR chemical shifts of 4 and the hypothetical brominated analogue.
Descriptors: Science Instruction, Spectroscopy, Scientific Concepts, College Science, Organic Chemistry, Undergraduate Study, Science Experiments, Inquiry, Science Laboratories, Computation, Laboratory Experiments
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation
Authoring Institution: N/A
Identifiers - Location: Minnesota; Wisconsin
Grant or Contract Numbers: CHE-0840494