SC CHEM 333 - Dehydration of Cyclohexanol to Cyclohexene Pre-Lab (6 pages)

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Dehydration of Cyclohexanol to Cyclohexene Pre-Lab



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Organic Chemistry 333L 03M Laboratory Pre Lab Dehydration of Cyclohexanol to Cyclohexene By Cameron Kahn 5 November 2013 TA James Collie 1 Page Objective In this experiment one will learn how to do an acid catalyzed dehydration of cyclohexanol into cyclohexene Then use fractional distillation to purify the product After purification identify the product using qualitative organic tests Intro Theory In an acid catalyzed dehydration an alcohol can proceed to change to an alkene This process is cause by a molecule of water is eliminated from a carbon compound This process is known to be called dehydration Dehydration is most commonly done through the means of heat and either the presence of phosphoric acid or sulfuric acid to catalyze the reaction Sciences In this lab one will use a secondary alcohol because they undergo dehydration easier than primary alcohols Handy A secondary alcohol requires much lower temperature to perform the acid catalyzed dehydration This will allow one to obtain the final product alkene much easier than the use of a primary alcohol In this experiment the reaction will undergo an E1 reaction This is due to the water molecule being eliminated from the two adjacent carbons The leaving group will leave first in order to create a carbocation in the molecule Therefore the first step is the slow rate determining step followed by a more rapid step Alkenes that form from this process are known to undergo alkene addition reactions In some instances these reactions can be used to determine the presence of an alkene in the final product In order to understand this theory look at Bromine for example Bromine is a brown liquid that turns clear with the presence of an alkene KMnO4 will form a brown precipitate 2 Page Mechanism Mechanism is a photocopy from the Chemistry lab manual written by George Handy Procedures Start by placing 0 9mL of water 1 2mL of 85 phosphoric acid 6 2mL of cyclohexanol and a boiling stone into a 25mL round bottom flask Next heat the



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