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Dehydration of Methylcyclohexanols

Page history last edited by jbfriesen 9 years, 2 months ago

Welcome to the dehydration of methylcyclohexanols page!

We are looking for collaborators to study this fascinating reaction.

2010 Student Handout Dehydration of 2-Methyl-1-cyclohexanol

Description of Collaborative Project: (Compilation of OChemOnline blog posts)

Student Handout: dehydration_of methylcyclohexanols_2008

This experiment was spun off into an undergraduate research project which was published in the Journal of Chemical Education - http://pubs.acs.org/doi/abs/10.1021/ed900049b

Summary of Procedure:

The dehydration of methylcyclohexanols is a variation of a popular organic chemistry lab.

The procedure is rather simple, but the diversity of products formed brings up some interesting discussion topics relating to the validity of the textbook understanding or E1 and E2 elimination reactions.

Positive aspects of this experiment: 

+ This simple dehydration reaction with hydrodistillation is a good introductory synthesis lab.

Neutral (may be positive or negative) aspects of this experiment: 

± Phosphoric acid has been the choice of mineral acid over the years. Perhaps it is less odorous and less dangerous than other options.

Negative aspects of this experiment:

- There is potential for loss of product during the liquid-liquid extraction and drying steps.

Inquiry & Extension Ideas:

● What will changing the reaction conditions do to the product distribution? In 2008 some student performed a 10 minute reflux before hydrodistilling off the alkenes.

 ● How will changing the acid affect product distribution?

Chromatograms/Spectra Links:

2010 GC-FID results

2010 IR results

2010 RI diagram

2007 GC-FID Chromatograms.pdf

Student Comments:

Student_Comments_2008: Dehydration of Methylcyclohexanols

Student_Comments_2007:_Dehydration of Methylcyclohexanols

Photo Gallery:

 

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