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ERIC Number: EJ1110417
Record Type: Journal
Publication Date: 2016-Aug
Pages: 6
Abstractor: As Provided
ISSN: ISSN-0021-9584
Investigating a Chemoselective Grignard Reaction in an Undergraduate Discovery Lab to Predict Reactivity and Final Products
Maher, Michael J.; Hayes, Colin O.; Vaccaro, Francesca A.; Flynn, Cailyn B.; Thedford, R. Paxton; Stephenson, Clifton J.
Journal of Chemical Education, v93 n8 p1464-1469 Aug 2016
A discovery-based Grignard experiment that emphasizes several important concepts in organic chemistry is reported. The Grignard reagent from 1- bromo-4-chlorobenzene was prepared and reacted with dimethylformamide (DMF) to synthesize 4-chlorobenzaldehyde. Students were tasked with predicting halogen reactivity in the formation of the Grignard reagent, predicting the final product, and drawing a reasonable mechanism for the reaction with DMF. The Grignard reaction with tertiary amides is typically not discussed in the organic chemistry curriculum, so the students have an opportunity to apply concepts covered in lecture to a new situation. Lastly, the students experimentally verified the identity of the product using thin layer chromatography, melting point analysis, gas chromatography, IR and NMR spectroscopy, and mass spectrometry.
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: N/A
Authoring Institution: N/A
Identifiers - Location: Louisiana (New Orleans)
Grant or Contract Numbers: N/A