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Dehydration of Menthol to Cycloalkenes John R. Griswold and Allegra Gravely* Cedar Crest College, Department of Chemistry, 100 College Dr., Allentown Pennsylvania 18104 It has been proposed that exo double bonds stabilize a 5-membered ring and destabilizes a 6-membered ring, and a sweeping statement6 has been made that reactions will proceed in such a manner as to avoid the construction or preservation of an exo double bond in a 6-membered ring. This theorem was verified in this case study, involving the dehydration of menthol.In this study, dl-menthol (Fisher Sci. Co. molecular weight 156g/mole) was treated with H3PO4, PCl3, and other dehydration agents, to determine alkene reaction products and reaction product ratios. Theoretically, if menthol was allowed to react with H3PO4, three possible cycloalkenes should be produced from the reaction as seen in Scheme 1. When 7.81 g (.05 moles) of Menthol was reacted with 10 mL of 85% H3PO4, the products and...

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