William Mason

Date of Award


First Advisor

David Myers

Second Advisor

Mike Bergman


This experiment was meant to investigate the chemical shift of the central hydrogen of 3,3-dinoradamantylmethane in a Hydrogen Nuclear Magnetic Resonance Spectroscopy experiment. The chemical shift of the central hydrogen of a similar compound, 1, 1 '-diadamantylmethane, is located at a position that, at first, appears unusual. The explanation of the shift delves deeper into NMR theory. Calculations place the hydrogen shift of the noradamantyl compound upfield of the adamantyl version. This thesis was meant to synthesize 3,3-dinoradamantylmethane so that the theory could be tested. The complete synthesis was planned out but due to difficulties along the way, the synthesis was not completed. Experiments in the lab ran into problems with yield, mixed products, and purity. Therefore, this Thesis became practice in organic synthesis for me. Even though the original goal was not achieved, I was able to gain valuable lab experience, and I was able to explain two of my favorite methods of spectroscopy, Infrared and Nuclear Magnetic Resonance.

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