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Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast
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Abstract
We describe an integrated set of experiments for the undergraduate organic laboratory that allows students to compare and contrast biological and chemical means of introducing chirality into a molecule. The racemic reduction of ethyl acetoacetate with sodium borohydride and the same reduction in the presence of a tartaric acid ligand are described, and a capillary gas chromatography column packed with a chiral material for product analysis is introduced. The results of these two hydride reactions are compared with the results of a common undergraduate experiment, the baker's yeast reduction of ethyl acetoacetate.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Chirality / Optical ActivityCiting Articles
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This article has been cited by 14 ACS Journal articles (5 most recent appear below).
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Animesh Aditya , David E. Nichols and G. Marc LoudonJournal of Chemical Education2008 85 (11), 1535This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly ...
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory
Eric Eby and S. Todd DealJournal of Chemical Education2008 85 (10), 1426A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory
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- Received: August 03, 2009
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