Lab 9a Chirality

Lab 9a Chirality - 9a Chirality Gas Chromatography and...

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9a Chirality, Gas Chromatography, and Menthone Author: Holly Polk Instructor: Oleksandr Zhurakovskyi Organic Chemistry Lab 243A, Section 010 Date Work Performed: April 2, 2009 Date Submitted: April 9, 2009 Abstract In this lab, the isomerization of (-)-menthone to (+)-isomenthone was performed. In this lab, (-)-menthone was combined with acetic acid and HCl and refluxed, then gas chromatography was performed. Gas chromatography works on the principle of boiling points and polarity, and peaks are eluted for different compounds. In relation to one another, the GC reading revealed that the sample had a 43/57% relation in favor of (-)- menthone. This is acceptable because the reaction of menthone and isomenthone is in equilibrium, so a specific ratio is not expected.
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Introduction In this lab, we used gas chromatography to determine the extent of (-)-menthone to (+)-isomenthone isomerization using reflux. This lab works on similar principles of column chromatography. In gas chromatography, the eluent used is helium, and the stationary phase is a high boiling liquid deposited on a solid substrate. The elution time is different based on boiling points and the polarity of the compound. Compounds with lower boiling points and less polar products elute first. The reaction scheme used within this lab shows that the isomerization process is dependent upon acidic conditions. When exposed to a hydronium rich environment, three main events occur: 1) ketone hydrogenation 2) double bond hydrogenation 3) alcohol dehydration. Throughout this process (-)-menthone is isomerized into (+)-isomenthone. Comparing both of these structures, one notices a striking similarity; both share chiral
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Lab 9a Chirality - 9a Chirality Gas Chromatography and...

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