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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > March  >
In the Laboratory
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment
Michael A. G. Berg
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA 24060-0212,

Roy D. Pointer
Department of Chemistry, Bloomsburg University, Bloomsburg, PA 17815
Cover
March 2007
Vol. 84 No. 3
p. 483

Abstract
A commercially available Grignard reagent (3.0 M solution of phenyl magnesium bromide in ether) was used in a convenient Grignard synthesis in a second-year organic chemistry laboratory without any of the typical failures associated with the Grignard reaction. The reaction setup used oven-dried glassware and no extraordinary measures were taken to keep the reaction under inert atmosphere. The Grignard reagent was dispensed into students' reaction vessels by the instructor. The students then slowly added a solution of a ketone. The yields of the resulting tertiary alcohols were good to excellent. Additional activities included determination of recrystallization solvent and characterization of their purified products using TLC, mp, IR, and NMR spectroscopy. This lab was used as the student's first exposure to a synthesis-type experiment and occurred early in the second-semester organic course corresponding to the lecture material concerning Grignard reactions.
Supplement
Detailed student instructions for the experiment and instructor's notes are available.
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Citation
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007 84 483.
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Keywords
Aldehydes / Ketones; Grignard Reagents; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Organometallics; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
2/1/2007
2/16/2007
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Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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