TY - JOUR
T1 - Investigating a Chemoselective Grignard Reaction in an Undergraduate Discovery Lab to Predict Reactivity and Final Products
AU - Maher, Michael J.
AU - Hayes, Colin O.
AU - Vaccaro, Francesca A.
AU - Flynn, Cailyn B.
AU - Thedford, R. Paxton
AU - Stephenson, Clifton J.
N1 - Publisher Copyright:
© 2016 The American Chemical Society and Division of Chemical Education, Inc.
PY - 2016/8/9
Y1 - 2016/8/9
N2 - 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.
AB - 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.
KW - Aldehydes/Ketones
KW - Grignard Reagents
KW - Inquiry-Based/Discovery Learning
KW - Laboratory Instruction
KW - Organic Chemistry
KW - Second-Year Undergraduate
KW - Upper-Division Undergraduate
UR - http://www.scopus.com/inward/record.url?scp=84981188237&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84981188237&partnerID=8YFLogxK
U2 - 10.1021/acs.jchemed.5b00453
DO - 10.1021/acs.jchemed.5b00453
M3 - Article
AN - SCOPUS:84981188237
SN - 0021-9584
VL - 93
SP - 1464
EP - 1469
JO - Journal of Chemical Education
JF - Journal of Chemical Education
IS - 8
ER -