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A Multistep Synthesis for an Advanced Undergraduate Organic Chemistry Laboratory
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Abstract
A three-step procedure appropriate for an advanced-level undergraduate organic chemistry laboratory course has been developed for the synthesis of 5-(2-sulfhydrylethyl)salicylaldehyde. Two compounds, namely, 4-(2-iodoethyl)phenol and 5-(2-iodoethyl)salicylaldehyde, are isolated as intermediates from the first two steps of the method. A Grignard reagent is employed as a critical reactant for the synthesis. Several important laboratory techniques, such as TLC, column chromatography, and recrystallization, are emphasized. Spectrometric methods, including GC–MS and NMR spectroscopy, are used to identify the final product as well as the intermediates. Since each step of the procedure involves two or more hours of refluxing, parts of this experiment can be interspersed with other laboratory activities.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Aromatic CompoundsCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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Rapid Multistep Synthesis of a Bioactive Peptidomimetic Oligomer for the Undergraduate Laboratory
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Identification of an Unknown Compound by Combined Use of IR, 1H NMR, 13C NMR, and Mass Spectrometry: A Real-Life Experience in Structure Determination
Louis J. Liotta and Magdalena James-PedersonJournal of Chemical Education2008 85 (6), 832Identification of an Unknown Compound by Combined Use of IR, 1H NMR, 13C NMR, and Mass Spectrometry: A Real-Life Experience in Structure Determination
Louis J. Liotta and Magdalena James-PedersonJournal of Chemical Education2008 85 (6), 832In this introductory organic chemistry experiment, the students get an opportunity to analyze and identify an unknown compound as it is done in a real-laboratory setting. First, students are instructed on the proper operation of three major instruments, ...
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- Received: August 03, 2009
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