David Hamilton '09 (Middleton, Mass.) is spending his summer in the lab working with chemicals. The rising sophomore has returned for the second year of his STEP/Dreyfus grant and is working under Ian Rosenstein, associate professor of chemistry. Hamilton's project is to synthesize free radical precursors to study the transition states of the cyclopropylcarbinyl radical ring opening reaction.
The cyclopropylcarbinyl rings react in a way that is counterintuitive in terms of how they open, when a radical (an unpaired electron) is generated adjacent to the rings. Other scientists have proposed an intermediate transition state between the rings, and Hamilton and Rosenstein are now trying to prove that this idea is accurate. They are, as Hamilton explains, "testing a theory that's out there."
The method of actually testing this theory is to build many forms of the cyclopropylcarbinyl ring molecule and examine how fast differentially substituted molecules react when they break apart. To do this, Hamilton is attempting to run his compounds through a six-step series of reactions and analyze the end product. Rosenstein's laboratory has been working on this project for some time now and Hamilton explains that the actual process has undergone a good deal of redesigning. However, "things look pretty hopeful," says Hamilton.
The hardest part of the project, Hamilton explains, is the frustration when something does not work as expected. "I've had to go back to the beginning [and] start from scratch a lot" he says, as for example now, when a familiar process has unexpectedly stopped working.
Hamilton worked last year in the computational chemistry lab of George Shields, the Winslow Professor of Chemistry. Returning for his second year of lab work, however, he "wanted to do wet chemistry." He finds the experience interesting and is certain that he wants to return next summer to do more research, though he is not sure where he would like to work. "I want to be a chemist," explains Hamilton, who is an undeclared chemistry major. He is a member of the Hamiltones, a campus a cappella group, and plays IM sports.
- Lisbeth Redfield
