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The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride
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Abstract
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 discovery oriented lab experiments that illustrate the chemoselective reduction of aldehydes in the presence of esters using NaBH4. The experiments involve the reduction of vanillin acetate and methyl 4-formylbenzoate, using sodium borohydride, followed by product identification using 1H and 13C NMR spectroscopy. Product identification is also achieved by classical qualitative functional group tests. The added element of discovery insures that student interest and enthusiasm are retained.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
NMR SpectroscopyCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Chemoselective Reactions of Citral: Green Syntheses of Natural Perfumes for the Undergraduate Organic Laboratory
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Anna D. Cunningham, Eun Y. Ham, and David A. VosburgJournal of Chemical Education2011 88 (3), 322-324Chemoselectivity is a central concept in organic synthesis and may be readily appreciated in the context of the fragrant, polyfunctional natural product citral. We describe three single-step reactions students may perform on citral to synthesize other ...
Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory
Animesh Aditya , David E. Nichols and G. Marc LoudonJournal of Chemical Education2008 85 (11), 1535Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory
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 Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Richard A. Kjonaas and Ryand J. F. TuckerJournal of Chemical Education2008 85 (1), 100A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Richard A. Kjonaas and Ryand J. F. TuckerJournal of Chemical Education2008 85 (1), 100The use of permanent magnet 13C NMR in large-section first-semester organic chemistry lab courses is limited by the availability of experiments that not only hinge on first-semester lecture topics, but which also produce at least 0.5 mL of neat liquid ...
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- Received: August 03, 2009
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