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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

J. Chem. Educ., 1998, 75 (1), p 85

DOI: 10.1021/ed075p85

Publication Date (Web): January 1, 1998

Section:

History, Education, and Documentation

Abstract

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Microscale Lab

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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Grignard Reactions in "Wet" Ether
David H. Smith
Journal of Chemical Education1999 76 (10), 1427
- Grignard Reactions in "Wet" Ether
  David H. Smith
  Journal of Chemical Education1999 76 (10), 1427
  A small laboratory ultrasonic bath can be used to initiate the Grignard reaction of alkyl or aryl bromides in regular laboratory-quality, undried, diethyl ether and in simple undried test tubes. The reaction typically starts within 30 to 45 seconds and is ...
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