Abstract
The mineral acid-catalyzed dehydration of 2-methyl-1-cyclohexanol has been a popular laboratory exercise in second-year organic chemistry for several decades. The dehydration experiment is often performed by organic chemistry students to illustrate Zaitsev’s rule. However, sensitive analytical techniques reveal that the results do not entirely corroborate with Zaitsev’s rule. Previous reports pertaining to this experiment have been limited by two factors: (i) it is difficult to separate 3- and 4-methyl-1-cyclohexene on a standard gas chromatography (GC) column and (ii) methods of accurate detection, identification, and quantification of trace minor products have been lacking. The current study uses gas chromatography–electron impact mass spectrometry (GC–MS) and quantitative nuclear magnetic resonance (qNMR) to identify and quantify not only the putative 1-, 3-, and 4-methyl-1-cyclohexene products but also several minor products such as methylenecyclohexane and ethylidenecyclopentane. Performing the dehyd...
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