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| Home > JCE Print > Journal of Chemical Education > Issues >
1998
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January
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In the Laboratory
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A Grignard-like Organic Reaction in Water
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Gary W. Breton and Christine A. Hughey
Berry College, Department of Chemistry, 2277 Martha Berry Blvd., P.O. Box 495016, Mount Berry, GA 30149-5016
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January 1998
Vol. 75 No. 1
p. 85
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| Abstract |
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The addition of a Grignard reagent to a carbonyl-containing compound to form an alcohol is an important reaction to demonstrate in organic chemistry laboratory courses. However, the reaction presents several practical problems for the lab instructor including the need for anhydrous solvents (e.g., ether), dry glassware, and the occasional problem of slow reaction initiation. We have scaled, and tested, a known Grignard-like reaction between allyl bromide and benzaldehyde mediated by zinc metal in aqueous media. The procedure retains the desirable features of the traditional Grignard reaction, while eliminating some of the commonly encountered difficulties. Thus, addition of allyl bromide (1.2 eq) to benzaldehyde and zinc in a two-phase mixture of THF and saturated aqueous NH4Cl afforded addition product 1-phenyl-3-buten-1-ol in 70-85% yields.
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| More Information |
 Citation |
Breton, Gary W.; Hughey, Christine A. J. Chem. Educ. 1998 75 85.
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Keywords |
Organic Chemistry, Laboratory Instruction, Microscale, and Organic Synthesis
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History |
Created:
Last Updated: |
June 28, 1999
June 23, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1998
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January
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85
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