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Reduction of Carboxylic Acids with Sodium Borohydride and an Electrophile

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Jan William Simek , Thad Tuck and Kelly Courter Bush

Department of Chemistry and Biochemistry, California Polytechnic State University San Luis Obispo, CA 93407

J. Chem. Educ., 1997, 74 (1), p 107

DOI: 10.1021/ed074p107

Publication Date (Web): January 1, 1997

Section:

History, Education, and Documentation

Abstract

Our goal was to develop the new reduction conditions into a procedure applicable to the first-year organic chemistry laboratory, where reduction of the carboxylic acid group has remained an obstacle, notwithstanding the use of borane or LiAlH₄ (2) on the microscale. The NaBH₄ method with either electrophile can be modified to any scale; in our hands, the use of I₂ as the electrophile performed better at the semimicro scale than the H₂SO₄ method.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carboxylic Acids

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

Synthesis of a New Ligand for Transition Metal−Fullerene Supramolecular Systems
Joel R. Deye, Amber N. Shiveley, Sean M. Goins, Lauren Rizzo, Stuart A. Oehrle, and Keith A. Walters
Inorganic Chemistry2008 47 (1), 23-25
- Synthesis of a New Ligand for Transition Metal−Fullerene Supramolecular Systems
  Joel R. Deye, Amber N. Shiveley, Sean M. Goins, Lauren Rizzo, Stuart A. Oehrle, and Keith A. Walters
  Inorganic Chemistry2008 47 (1), 23-25
  A new substituted fullerene is presented that can easily be introduced into other -conjugated supramolecular systems using basic coupling methods. The substituted fullerene is linked to a rhenium transition-metal chromophore through a bipyridine ligand, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride
Ashvin R. Baru and Ram S. Mohan
Journal of Chemical Education2005 82 (11), 1674
- The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride
  Ashvin R. Baru and Ram S. Mohan
  Journal of Chemical Education2005 82 (11), 1674
  Chemoselective reductions are valuable in organic synthesis and are routinely discussed in a sophomore organic chemistry course. Yet, there are very few examples of laboratory experiments that illustrate such chemoselectivity. We have developed two ...
  Abstract | Hi-Res PDF | PDF w/ Links