Robert Simack, Department of Chemistry and Biochemistry, University of Alaska Fairbanks, Fairbanks, Alaska.

Abstract: This study involved acid dehydration of 2-methylcyclohexanol. The results varied depending on the time elapsed after initial reaction. I attempted to prove the Evelyn Effect, which stated that over a period of time the products of the aforementioned reaction will beobserved to change volume so that those products formed by a cis isomer of 2-methylcyclohexanol will form first. However, once all molecules in the cis isomer undergo reaction the remaining trans configured 2-methylcyclohexanols will proliferate during the latter period of the reaction. I also postulated as to the possible formulation of 1-ethylcyclopentene, and to the cause of such an event.

Introduction: After researching acid-catalyzed dehydration reactions (McMurray) and background on the Evelyn Effect (Clausen) I hypothesize that the cis isomer of 2-methylcyclohexanol will react via an E1 type process forming 1-methylcyclohexene according to predictions from Zaitzev's rule (Lehman). This should be due to the fact that the cis isomer has 2 anti-coplanar hydrogens. T

Also, peaks for 1-ethylcyclopentene begin to show in the spectra for the second fraction and increase in size (area beneath the peak) by the spectra of the third fraction. At the root of this phenomena is steric hinderance. Both the cis and trans isomers will form 1-ethylcyclopentene (fig. 1). However, because of steric hinderance the trans isomer is favored to form the 1-ethylcyclopentene. This fact will explain why more of the pentene shows up in the third fraction.

Experimental: An apparatus was constructed with a round bottom flask topped by a claisen adaptor in which was placed a thermometer and a condensing tube. In the apparatus 150mmole of 2-methylcyclohexanol was mixed with 5mL H3PO4 and distilled. The distilled liquid was collected in three tubes, at approximately 4mL per tube, labeled fraction 1, 2 and 3. Each fraction was placed in a centrifuge tube and combined with 4mL saturated NaHCO3. The aqueous layer was removed and MgSO4 was added for a final separation. The solid and aqueous layers were then removed and the final product was combined with CDCL3 in an NMR tube in preparation for spectra. The liquid remaining in the original apparatus was put through the separation process described above. However, instead of CDCL3 as a spectrum reagent we used CH2CL2. Also, an NMR was not performed on the remaining liqui

Some common words found in the essay are:
Standish NMR, Effect Clausen, Evelyn Effect, Discussion NMR, CDCL3 NMR, Alaska Abstract, Organic Chemistry, GC Figure, cis isomer, CH2CL2 NMR, cis trans, trans isomers, cis trans isomers, Fairbanks March, third fraction, spectra fraction, organic chemistry, starting material, cis isomer 2-methylcyclohexanol, form 1-ethylcyclopentene, fraction cis, trans isomer, fraction cis isomer, spectra third fraction,
Approximate Word count = 907
Approximate Pages = 4 (250 words per page double spaced)