Ask and you shall receive – Reflections on the first semester and a half

Find the grad student!After a little kick in the pants from Joel, I’ve decided to start updating this thing again. I know all you loyal readers are just dying for the latest juicy tidbits of my life, so why waste time with pleasantries? Let’s get right into it. I’d like to divide this post into two sections: “What I’ve Learned” and “What I’ve Had to Unlearn” in graduate school.

What I’ve Learned
1. Chemistry is 85% attitude, 10% luck, and 5% hard work. Yes, the world of chemistry is hopelessly enormous. And yes, much of the modern literature, due to the ridiculous pace of science in today’s world, could potentially be construed as complete bullshit. Having the right attitude towards these dismal facts is over half the battle, however. And strangely, where I once felt hopeless and defeated, a twinkle of optimism now resides.
2. There are enough variants of the aldol reaction to keep a gaggle of graduate students busy for days.
3. Seminar speakers can be as bad (or worse) as graduate students at public speaking.
4. Basically, outside of industry, there are no scientists other than graduate students. When you enter graduate school, you are immediately considered a professional scientist – and this is both exciting and utterly petrifying at the same time.
5. Failure is OK, as long as you think about how and why you (or, I should say, your chemistry) failed.
6. Students will believe whatever you say, as long as you sell it. And selling chemistry is close to the most fun I can have in any given hour (close :-D). To any former students who are reading this, I was never wrong. NEVER.

What I’ve Had to Unlearn
1. Huckel theory. I know this is probably going to elicit a collective “WTF?” from the chemists in the audience, but there are a number of compelling arguments against applying Huckel theory to pi bonding and lone-pair resonance. The Burgi-Dunitz angle, for example, is explained perfectly by Pauling’s “tau-bonding” model, which involves the mixing of all four atomic orbitals on carbon (instead of the usual three) to produce the hybrid orbitals of a singly unsaturated carbon (viz., a double bond). The tau-star orbital of the carbonyl group is oriented at almost exactly the Burgi-Dunitz angle, ripe for attack by an incoming nucleophile. The tau bonding model also helps explain the non-planarity of enamines, which has been supported independently by x-ray studies. Check out pages 166-167 of this link for an intro.
2. There is such a thing as asymmetric alkylation of enolates. For some reason, and God knows why, I was all about this imaginary reaction in undergrad. But aside from the Myers alkylation and other auxiliary-based methods, it’s still an unsolved problem. SOMO catalysis may solve it soon though…
3. School is a competition. This gets beaten out of you early in grad school. Finally, I think, in graduate school “the man” trusts you to use school for actual learning, and not as a means of differentiation or specialization. And if, after a semester and a half of graduate school, you still think you’re involved in a competition with your fellow students, well…good luck with that Dear John letter.

Happy late Valentine’s Day everyone!



  1. Well played, sir.

    Learned: Make sure #1 stays true (the optimism part) as long as you can. Also, it may be more like 85% attitude, 10% luck, and 64% hard work [sic]

    Unlearned: Always, always remember #3. More true than you know yet. Keep this in mind for awards, fellowships and exit strategies.


  2. yesssss! i feel giddy with my newfound power over the blogosphere. thanks for the great post! next i shall ask ye to fashion me a crown and sceptre out of pyrex glassware and stirbars.

    2nding the immense requirement for staying optimistic. for a time last semester, i had to have my google calendar email me every day with a reminder that i am awesome. as silly as that sounds, it always seemed to bring a smile to my face.


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