The Joys of Being a Chemistry Student

(first published Aug 20, 2008)

My first genuine taste of organic chemistry came in my sophomore year
of college (73-74). I studied from a large (1000 page) textbook not too
different from yours. There was a lot to remember, but I was doing
alright until the second quarter when a subtle and unannounced change
in the book quite threw me.
This “change” appeared when we began studying the chemical reactions of
alkenes, our first “reaction” chapter. I had read the entire chapter
and I had not had any trouble following the formulas and explanations,
yet I was completely stymied by the end-of-chapter problems. I looked
at one problem after another, but I couldn’t find even one that I could
answer. I couldn’t even start an answer (and going back to look at the
chapter, something that I hated doing, didn’t help one bit). I don’t
recall what went through my head, but I felt profoundly incompetent
because, just a week earlier, I had been doing very well.

In
those days we didn’t have solution manuals so I decided to walk across
campus to find the lab where the TA who ran my weekly problem session,
a graduate student, was working on his doctoral research. Being a nice
guy, but perhaps also because he was surprised that any of his 16-odd
students had actually found his dingy third-floor lab, he was more than
willing to help. We found a well-used chalkboard in one corner of the
lab and he talked me through a couple of the “what reagent will turn A
into B?” and “what do you get when you combine A and B?” questions that
had been stumping me. After about 20 or 30 minutes, I realized I was
starting to get the hang of it, but that I didn’t have any of the
background information I needed to work these problems on my own. I
would need to reread the entire chapter. More importantly, I would need
to read it differently this time because, even though the words and
formulas had gone into my head, nothing had stuck. I couldn’t look at a
problem and say, “oh yeah, I remember seeing something just like that.”
So, I headed back to my room, sat down with my book and a pencil and
started to reread the chapter, writing and drawing formulas as I went.
My problems didn’t magically vanish. In fact, “studying” o chem had
just gotten a lot harder and more time-consuming, but for a while, at
least, I wasn’t stuck and I knew where to go for help the next time.

The
o chem lab was another interesting place. My first assignment was to
convert benzene, a smelly liquid, into benzophenone, a crunchy white
crystalline solid. I don’t recall being given much advance information
beyond two pages of instructions that contained many words I didn’t
understand (“reflux”? “rotovap”?), warnings that scared the begeezus
out of me (“benzene is a cumulative liver poison”), and a drawing of an
impressive-looking apparatus. I was clearly lost, but it didn’t occur
to me to go find a TA, so I decided that when I got to lab I would look
for someone who looked like they knew what they were doing and I would
copy everything they did.

My Follow-the-Leader strategy worked
fairly well for about two hours, at which point a (different) TA came
along, looked at my apparatus, and said, “you can stop that and work it
up.” I was happy to stop, but when I looked around the lab, I
discovered to my consternation that everyone else was still boiling
their reaction mixtures. I was going to have to go it alone. Since I
still couldn’t make heads-or-tails of the remaining instructions, I
decided the only practical option was to slow waaaay down, give my lab
mates a chance to catch up, and then play Follow-the-Leader again. In
fact, I only needed to fiddle around for about 10 minutes before they
had caught up and everything started rolling along smoothly again until
I reached the last step: evaporating the solvent from my product.
Instead of being left with a white solid residue like everyone else
(this was actually the point at which I learned that benzophenone was a
white solid), I was left with a colorless liquid. I showed the liquid
to the TA, who remarked, “oh, your product oiled out” (apparently my
“liquid” was now an “oil”) and went on, “let me get you a seed
crystal.” I stood there puzzled, but patient, holding the flask that
contained the liquid/oil until he returned with a small vial containing
white crystals and a spatula. He carefully transferred one or two tiny
crystals from his vial to my “oil”, whereupon the entire mass instantly
solidified. He smiled and said, “there you go” and I was relieved that
this sudden amazing transformation had solved all my problems, for a
week anyway.