Chem 243a - Chirality, Gas Chromatography and Menthone

Chem 243a - Chirality, Gas Chromatography and Menthone -...

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9A: Chirality, Gas Chromatography and Menthone Antonio Alarcon Chem 243a 10/29/07 I. Abstract In this lab, the isomerization of (-)-menthone to (+)-isomenthone was performed. The end product had a 60/40% relation in favor of (+)-isomenthone to (-)-menthone.
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II. Introduction In this lab, we were to use gas chromatography to determine the extent of (-)-menthone to (+)- isomenthone isomerization. This was accomplished in a process similar to the previous lab in which refluxing played a critical role. Apparent by the reaction scheme employed within this lab, the isomerization process is dependent upon acidic conditions. When exposed to an 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 centers as well as contain a plane of symmetry. Because of this similarity, (-)-menthone and (+)-isomenthone are recognized as enantiomers. Yet, unlike enantiomers with one chiral center, the molecules observed in this lab have two chiral centers, thus yielding four possible stereoisomers. Due to the fact that (-)- menthone and (+)-isomenthone are enantiomers, one would assume the same holds for the additional
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This note was uploaded on 04/03/2008 for the course CHEM 243A taught by Professor Bharadwaj during the Fall '08 term at University of Arizona- Tucson.

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Chem 243a - Chirality, Gas Chromatography and Menthone -...

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