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Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment

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Roy D. Pointer

Department of Chemistry, Bloomsburg University, Bloomsburg, PA 17815

Michael A. G. Berg

Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA 24060-0212,

J. Chem. Educ., 2007, 84 (3), p 483

DOI: 10.1021/ed084p483

Publication Date (Web): March 1, 2007

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aldehydes / Ketones

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

The Question-Driven Laboratory Exercise: A New Pedagogy Applied to a Green Modification of Grignard Reagent Formation and Reaction
Jennifer M. Teixeira, Jessie Nedrow Byers, Marilu G. Perez and R. W. Holman
Journal of Chemical Education2010 87 (7), 714-716
- The Question-Driven Laboratory Exercise: A New Pedagogy Applied to a Green Modification of Grignard Reagent Formation and Reaction
  Jennifer M. Teixeira, Jessie Nedrow Byers, Marilu G. Perez and R. W. Holman
  Journal of Chemical Education2010 87 (7), 714-716
  Experimental exercises within second-year-level organic laboratory manuals typically involve a statement of a principle that is then validated by student generation of data in a single experiment. These experiments are structured in the exact opposite ...
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