Dehydration of 2-methylcyclohexanol edited.docx - Dehydration of 2-methycyclohexanol Lead Author Justin Upshaw Reviewer Christian Lamb Editor Josh Lance

Dehydration of 2-methylcyclohexanol edited.docx -...

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Dehydration of 2-methycyclohexanol Lead Author: Justin Upshaw Reviewer: Christian Lamb Editor: Josh Lance
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Introduction Zaitsev’s rule states that in an elimination reaction the most substituted product will generally be the most favored. As alkene substitution increases, so does alkene stability. Therefore, in the experiment the alkene formed that is the most substituted will be the major product of this reaction. An acid catalyzed dehydration occurs when an alcohol is heated in the presence of catalytic acid, which causes water to leave and an alkene is formed. The OH group of the alcohol will be protonated by the alcohol and leave as water, forming a secondary carbocation. Since 2- methylcyclohexanol is unimolecular, it will continue with an E1 mechanism. Water will act as a base and remove the hydrogen at the β -position. The electrons in the carbon-hydrogen bond will shift toward the carbocation carbon, forming an alkene. Gas chromatography is a useful way to determine product purity and relative abundance of product(s). The process uses a gas chromatograph that uses a slow heating oven to vaporize the sample. The machine will record the time it took for each product to be vaporized and this will be referred to as the “retention time”. Since products with lower boiling points will evaporate first, it will show the relative abundance of each product formed and their retention time.
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