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
\nalkenes, our first “reaction” chapter. I had read the entire chapter
\nand I had not had any trouble following the formulas and explanations,
\nyet I was completely stymied by the end-of-chapter problems. I looked
\nat one problem after another, but I couldn’t find even one that I could
\nanswer. I couldn’t even start an answer (and going back to look at the
\nchapter, something that I hated doing, didn’t help one bit). I don’t
\nrecall what went through my head, but I felt profoundly incompetent
\nbecause, just a week earlier, I had been doing very well.<\/p>\n
In
\nthose days we didn’t have solution manuals so I decided to walk across
\ncampus to find the lab where the TA who ran my weekly problem session,
\na graduate student, was working on his doctoral research. Being a nice
\nguy, but perhaps also because he was surprised that any of his 16-odd
\nstudents had actually found his dingy third-floor lab, he was more than
\nwilling to help. We found a well-used chalkboard in one corner of the
\nlab and he talked me through a couple of the “what reagent will turn A
\ninto B?” and “what do you get when you combine A and B?” questions that
\nhad been stumping me. After about 20 or 30 minutes, I realized I was
\nstarting to get the hang of it, but that I didn’t have any of the
\nbackground information I needed to work these problems on my own. I
\nwould need to reread the entire chapter. More importantly, I would need
\nto read it differently this time because, even though the words and
\nformulas had gone into my head, nothing had stuck. I couldn’t look at a
\nproblem and say, “oh yeah, I remember seeing something just like that.”
\nSo, I headed back to my room, sat down with my book and a pencil and
\nstarted to reread the chapter, writing and drawing formulas as I went.
\nMy problems didn’t magically vanish. In fact, “studying” o chem had
\njust gotten a lot harder and more time-consuming, but for a while, at
\nleast, I wasn’t stuck and I knew where to go for help the next time.<\/p>\n
The
\no chem lab was another interesting place. My first assignment was to
\nconvert benzene, a smelly liquid, into benzophenone, a crunchy white
\ncrystalline solid. I don’t recall being given much advance information
\nbeyond two pages of instructions that contained many words I didn’t
\nunderstand (“reflux”? “rotovap”?), warnings that scared the begeezus
\nout of me (“benzene is a cumulative liver poison”), and a drawing of an
\nimpressive-looking apparatus. I was clearly lost, but it didn’t occur
\nto me to go find a TA, so I decided that when I got to lab I would look
\nfor someone who looked like they knew what they were doing and I would
\ncopy everything they did.<\/p>\n
My Follow-the-Leader strategy worked
\nfairly well for about two hours, at which point a (different) TA came
\nalong, looked at my apparatus, and said, “you can stop that and work it
\nup.” I was happy to stop, but when I looked around the lab, I
\ndiscovered to my consternation that everyone else was still boiling
\ntheir reaction mixtures. I was going to have to go it alone. Since I
\nstill couldn’t make heads-or-tails of the remaining instructions, I
\ndecided the only practical option was to slow waaaay down, give my lab
\nmates a chance to catch up, and then play Follow-the-Leader again. In
\nfact, I only needed to fiddle around for about 10 minutes before they
\nhad caught up and everything started rolling along smoothly again until
\nI reached the last step: evaporating the solvent from my product.
\nInstead of being left with a white solid residue like everyone else
\n(this was actually the point at which I learned that benzophenone was a
\nwhite solid), I was left with a colorless liquid. I showed the liquid
\nto the TA, who remarked, “oh, your product oiled out” (apparently my
\n“liquid” was now an “oil”) and went on, “let me get you a seed
\ncrystal.” I stood there puzzled, but patient, holding the flask that
\ncontained the liquid\/oil until he returned with a small vial containing
\nwhite crystals and a spatula. He carefully transferred one or two tiny
\ncrystals from his vial to my “oil”, whereupon the entire mass instantly
\nsolidified. He smiled and said, “there you go” and I was relieved that
\nthis sudden amazing transformation had solved all my problems, for a
\nweek anyway.<\/p>\n","protected":false},"excerpt":{"rendered":"
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