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ERIC Number: EJ1062162
Record Type: Journal
Publication Date: 2015-Mar
Pages: 5
Abstractor: As Provided
Reference Count: 9
ISSN: ISSN-0021-9584
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.
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:; Web site:
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