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The Acid Catalyzed Dehydration of an Isomeric 2-Methylcyclohexanol Mixture: A Kinetic and Regiochemical Study of the Evelyn Effect
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Abstract
This paper details an experiment which serves as an introduction to organic laboratory research. The reaction is the dehydration of a cis, trans mixture of 2-methylcyclohexanols. At intervals of times the reactant mixture is sampled for the cis and trans reactants. At those same intervals of times the receiver flasks of product cyclohexanes being collected are changed, such that sequential fractions of material are obtained.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
CatalysisCiting Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Dehydration of 2-Methyl-1-cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment
J. Brent Friesen and Robert SchretzmanJournal of Chemical Education2011 Article ASAPDehydration of 2-Methyl-1-cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment
J. Brent Friesen and Robert SchretzmanJournal of Chemical Education2011 Article ASAPThe mineral acid-catalyzed dehydration of 2-methyl-1-cyclohexanol has been a popular laboratory exercise in second-year organic chemistry for several decades. The dehydration experiment is often performed by organic chemistry students to illustrate ...

Dehydration of Methylcyclohexanol Isomers in the Undergraduate Organic Laboratory and Product Analysis by Gas Chromatography−Mass Spectroscopy (GC−MS)
Malgorzata M. Clennan and Edward L. ClennanJournal of Chemical Education2011 88 (5), 646-648Dehydration of Methylcyclohexanol Isomers in the Undergraduate Organic Laboratory and Product Analysis by Gas Chromatography−Mass Spectroscopy (GC−MS)
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 ...

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 ...

Solving the Mathematics of a Kinetic and Regiochemical Problem: The Dehydration Reaction of a cis-trans Mixture of 2-Methylcycloalkanols
John J. CawleyJournal of Chemical Education1999 76 (1), 58Solving the Mathematics of a Kinetic and Regiochemical Problem: The Dehydration Reaction of a cis-trans Mixture of 2-Methylcycloalkanols
John J. CawleyJournal of Chemical Education1999 76 (1), 58A take-home exam is presented. It is based on an experiment that studied the dehydration of a cis-trans mixture of 2-methylcyclohexanols. The "givens" are the idealized kinetic and regiochemical data. The focus is strictly on the mathematics, not the ...
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History
- Received: August 03, 2009
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