Source: Vy M. Dong and Faben Cruz, Department of Chemistry, University of California, Irvine, CA
This experiment will demonstrate how to properly carry out a Grignard reaction. The formation of an organometallic reagent will be demonstrated by synthesizing a Grignard reagent with magnesium and an alkyl halide. To demonstrate a common use of a Grignard reagent, a nucleophilic attack onto a carbonyl will be performed to generate a secondary alcohol by forming a new C-C bond.
1. Grignard Reagent Formation
The purified product should have the following 1H NMR spectrum: 1H NMR δ 7.23-7.39 (m, 5H), 6.60 (d, J = 16.0 Hz, 1H), 6.23 (dd, J = 6.4 Hz, 1H), 5.84 (m, 1H), 5.14-5.20 (m, 2H), 4.35 (q, J = 6.4 Hz, 1H), 2.37-2.43 (m, 2H), 1.9 (br s, 1H).
This experiment has demonstrated how to synthesize a Grignard reagent from an aryl/alkyl halide and how to use the Grignard reagent to perform a nucleophilic addition onto a carbonyl compound to construct a new carbon-carbon bond.
The Grignard reaction is widely applied in the synthetic chemistry world, and is used in university research labs, national laboratories, and pharmaceutical companies. Simple Grignard reagents are commercially available, but often times unique and specialized Grignar
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