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Mass Spectral Fragmentation Patterns of Deuterated Butyl and Ethyl Acetates: An Easy Microscale Isotopic Labeling Experiment
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Abstract
We have developed an experimentally uncomplicated microscale second-semester organic lab exercise that illustrates the use of isotopic labeling, in this case deuteration, to help confirm and interpret mass spectral fragmentation patterns in butyl acetate and ethyl acetate. Preparation and gas chromatographic-mass spectrometric (GC-MS) analysis of unlabeled and labeled esters is followed by pooling of student data for interpretation and write-up.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
ChromatographyCiting Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis
Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2007 84 (10), 1679Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis
Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2007 84 (10), 1679The nitration of six benzene derivatives having a range of substituents that differ in electronic effects were followed by GC–MS analyses of the crude reaction mixtures and adapted for the second-year organic laboratory. Students pool their results and ...
The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory
Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2005 82 (11), 1676A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory
Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2005 82 (11), 1676An experiment suitable for adoption for first-semester organic laboratory is presented. The experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also ...
Deuterium Exchange in Ethyl Acetoacetate: An Undergraduate GC–MS Experiment
C.D. Heinson , J. M. Williams , W. N. Tinnerman and T. B. MalloyJournal of Chemical Education2005 82 (5), 787Deuterium Exchange in Ethyl Acetoacetate: An Undergraduate GC–MS Experiment
C.D. Heinson , J. M. Williams , W. N. Tinnerman and T. B. MalloyJournal of Chemical Education2005 82 (5), 787A simple experiment involving deuterium exchange of the enolizable protons in ethyl acetoacetate followed by GC–MS has been developed. The principles demonstrated are the use of stable isotopes, keto–enol tautomerism, base catalysis, and the use of ...
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- Received: August 03, 2009
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