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A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory
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Abstract
An 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 provides students with added experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
IR SpectroscopyCiting Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Dehydration of Methylcyclohexanol Isomers in the Undergraduate Organic Laboratory and Product Analysis by Gas Chromatography−Mass Spectroscopy (GC−MS)
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Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2011 88 (5), 646-648Dehydrations of cis- and trans-2-methylcyclohexanol mixtures were carried out with 60% sulfuric acid at 78−80 °C as a function of time and the products were identified by gas chromatography−mass spectroscopy (GC−MS) analysis. The compounds identified in ...
Counterion Effects in the Nucleophilic Substitution Reaction of the Acetate Ion with Alkyl Bromides in the Synthesis of Esters
Elizabeth M. Valentín and Ingrid Montes , Waldemar AdamJournal of Chemical Education2009 86 (11), 1315Counterion Effects in the Nucleophilic Substitution Reaction of the Acetate Ion with Alkyl Bromides in the Synthesis of Esters
Elizabeth M. Valentín and Ingrid Montes , Waldemar AdamJournal of Chemical Education2009 86 (11), 1315Esters are often employed as artificial flavorings in foods and drinks, since the more volatile ones possess distinctive odors characteristic of common fruits. The present laboratory experiment introduces students to the esterification method in which a ...
A Simple SN2 Reaction for the Undergraduate Organic Laboratory
John J. Esteb , John R. Magers , LuAnne McNulty , Paul Morgan and Anne M. WilsonJournal of Chemical Education2009 86 (7), 850A Simple SN2 Reaction for the Undergraduate Organic Laboratory
John J. Esteb , John R. Magers , LuAnne McNulty , Paul Morgan and Anne M. WilsonJournal of Chemical Education2009 86 (7), 850A simple procedure for the synthesis of n-butyl naphthyl ether is presented. This procedure represents an easy method for the production of an aryl ether by an SN2 reaction, uses ethanol as an environmentally friendly solvent, and does not require the use ...
A Safer, Discovery-Based Nucleophilic Substitution Experiment
Gail HorowitzJournal of Chemical Education2009 86 (3), 363A Safer, Discovery-Based Nucleophilic Substitution Experiment
Gail HorowitzJournal of Chemical Education2009 86 (3), 363A discovery-based nucleophilic substitution experiment is described in which students compare the reactivity of chloride and iodide ions in an SN2 reaction. This experiment improves upon the well-known "Competing Nucleophiles" experiment in that it does ...
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 ...
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- Received: August 03, 2009
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