There are a couple of things about the second semester of organic chemistry that I figured I would offer some comments on.
First, the number of reactions seem to be rather large – things like the Swern reaction, the Dess-Martin reaction, and so forth. It seems a little bit daunting at first, but the mechanisms for a lot of them are basically the same, or very similar. So, it would seem, that focusing on mechanism is important. But, there’s a snag. As we’ve started wading into the real world of organic chemistry, we’ve had to realize that a lot of the mechanisms for these reactions are not well-understood. Our textbook makes some comments about a particular reaction leading to a particular product, but doesn’t attempt to show the mechanism. This is a little bit frustrating, so it would be nice if our professor would tell us which reactions have mechanisms that are within our ability to understand and which aren’t well-understood.
A second thought is on NMR and spectroscopy. The physics behind how these techniques work isn’t all that difficult to understand. But, understanding the physics of something like NMR does not necessarily lead to being able to interpret data from NMR experiments or having a clue how these techniques work in the lab. Understanding simple spectra is relatively easy – the complicated ones are much more difficult to answer, and our professor seems to think that we should have a lot of intuition on interpreting these things. I suspect that sort of intuition is developed by spending years working in a lab as an organic chemist. It can be frustrating, and it’s not immediately clear to me how to improve at interpreting NMR and spectroscopic data. This is a little bit worrisome, since he seems to really like this stuff, which I guess isn’t all that surprising since he was an organic chemist for years before coming to academia.