Cyclic alcohols can undergo dehydration to produce cyclic alkenes. Such reactions are common undergraduate organic chemistry laboratory experiments and produce alkenes that are useful starting materials in organic synthesis reactions. In this research, several cyclic alcohols, such as 4-methylcyclohexanol and 3,3,5-trimethylcyclohexanol, were converted to cyclic alkene derivatives via acid-catalyzed dehydration using concentrated phosphoric acid. The final alkene products were purified by fractional and simple distillation and analyzed by gas-chromatography-mass spectrometry (GC-MS), micro boiling point, and refractive index. The major and minor isomeric alkene products were characterized by analyzing gas chromatogram peaks and fragmentation patterns of mass spectra. Mechanisms of isomerization were evaluated, including carbocation rearrangements, hydride shifts, and methyl shifts. Micro boiling point temperatures, refractive index values, and GC-MS spectra for each sample were then compared to theoretical data of the major product of each sample.

Gas chromatography-mass spectrometry (GC-MS) analysis of products obtained from the dehydration of cyclic alcohol derivatives

ACS Spring 2022

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