Date of Award




First Advisor

Dr. Michael Nichols


Carbocation rearrangements are particularly interesting mechanistic steps in organic reactions. Carbocations form when a carbon atom within a molecule is electron deficient, giving it a positive charge. A rearrangement occurs when either a hydrogen atom or methyl group from an adjacent carbon atom in the molecule moves to the carbocation, thus moving the carbocation to the adjacent carbon. This rearrangement only occurs if the newly formed carbocation is more stable than the previous carbocation. These concepts are typically taught in organic chemistry courses. Researchers from Villanova University, the University of Wisconsin-River Falls, and Bethel University designed an experiment to help students understand these concepts in experimental reactions with the use of spectroscopy.(1) However, in their experiment, they were unable to propose a mechanism for the formation of 2-bromo-3-methylbutane from neopentyl alcohol. This research proposes and confirms a mechanism for the formation of that product.

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