Saturday, February 16, 2013

ACID CATALYZED DEHYDRATION OF 2-METHYL-2-BUTANOL

Hey guys so we did this synthesis experiment in lab and I wanted to share it with you:

An acid catalyzed dehydration of 2-methyl-2-butanol was performed to produce a mixture of isomeric alkenes: 2-Methyl-1-butene and 2-methyl-2-butene. The product was characterized by taking the IR spectrum of it, and the exact ratio of the each isomer present in the product was calculated form the NMR spectrum giving a percent ratio of 20% for the isomer  2-Methyl-1-butene and 80% for 2-methyl-2-butene which supports our prediction in which the dominant or major product would be the 2-methyl-2-butene because of its more conjugated alkene that is more stabilized that the primary alkene in the second (minor) product 2-Methyl-1-butene.

Using ChemDraw I did the mechanism of the reaction, and it's as follows:
 

The procedure of the experiment was adapted from:  K.L. Williamson, “Organic Experiments”, 9th ed., Houghton Mifflin, 2004. 
Article on SciFinder pertaining to the reaction: https://scifinder.cas.org/scifinder/view/scifinder/scifinderExplore.jsf 

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