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Side Reactions in a Grignard Synthesis

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Hilton M. Weiss

Bard College, Department of Chemistry, Annandale-on-Hudson, NY 12504

J. Chem. Educ., 1999, 76 (1), p 76

DOI: 10.1021/ed076p76

Publication Date (Web): January 1, 1999

Abstract

This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Mechanisms of Reactions

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

Synthesis of 5,5-Diphenyl-4-penten-2-one: A Variation on a Classic Organic Synthesis Laboratory
Joshua P. Alber, Michael J. DeGrand, and Diana M. Cermak
Journal of Chemical Education2011 88 (1), 82-85
- Synthesis of 5,5-Diphenyl-4-penten-2-one: A Variation on a Classic Organic Synthesis Laboratory
  Joshua P. Alber, Michael J. DeGrand, and Diana M. Cermak
  Journal of Chemical Education2011 88 (1), 82-85
  The Grignard reaction and the addition of protecting groups are standard reactions in an organic chemistry course. Organic students learn about the “quench” step of the Grignard reaction using acid and water and the acid-catalyzed hydrolysis to remove the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course
James A. Ciaccio , Roxana P. Bravo , Antoinette L. Drahus , John B. Biggins , Rosalyn V. Concepcion and David Cabrera
Journal of Chemical Education2001 78 (4), 531
- Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course
  James A. Ciaccio , Roxana P. Bravo , Antoinette L. Drahus , John B. Biggins , Rosalyn V. Concepcion and David Cabrera
  Journal of Chemical Education2001 78 (4), 531
  We have developed an undergraduate organic laboratory experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive α-chiral ketone. Students isolate a single diastereomer of (+/-)-1,2-diphenyl-1,2-...
  Abstract | Hi-Res PDF | PDF w/ Links