Pushing the Envelope

When I was taking organic chemistry as a sophomore, the lecturing professor encouraged students to ask questions in his class.  His reason?  “If you have a question about something, chances are that someone else in the class has the same question.”  Likewise, I believe in open communication, particularly in learning the rudiments of organic chemistry.  Anyone who has taken a class with me will instantly recognize my trademark closing inquiry: “does anyone have any questions, comments or concerns.”  I give students one last chance to bring up any issues before the lab begins.  Usually, 95% of the time you can clearly hear a pin dropping on cotton during this time. 

The problem I’ve encountered over the past couple of years is the lack of preparedness by the average student.  Granted, the procedures will deviate from what’s in the book on occasion, but these concerns are addressed either in the prelab lecture or in my final instructions right as the lab period begins; I also leave notes about these issues on the whiteboard.  Remember the old cliché, “there’s no such thing as a stupid question”?  Some students recidivistically abuse this rule to the point of criminality.  Here are a few conversations between students (S) and teaching assistants (TA) over the past few years of teaching organic chemistry.  I’m sure you can supply your own examples.


S:            “I spilled my product in the hood.  What should I do?”

TA:         “A celebratory dance?”


S:             “My book says to add…um…sodium…brine…when the color changes.  Do I add it?” 

TA:          “Did the color change?” 

S:             Pause.  Smile.  “Yeah.” 

TA:          “Congratulations!  You answered your own question.  You’re one step closer to being a synthetic organic chemist.”

S:             “No.  This is my last semester of chemistry.”

TA:          “Really?”


S:             “What’s the molecular weight of anisole?”

TA:          “What’s the chemical formula?”

S:             “C…9…8…7…H…”

TA:          “What does your book say?”

S:             “I didn’t bring it.”


S:            “Can I go to the bathroom?”

TA:         “You’re in college.  You can do whatever you want.”

S:            “So, I don’t have to do the lab if I don’t want to?”

TA:         “I don’t care.”

S:            “So you’ll gimme an A?”

TA:         “No, I don’t care if you do the lab or not.  But you have to do the lab to get an A.”

S:            “That’s not fair.”


S:             “The book says use ‘dichloromethane,’ but there isn’t any in the hood.”

TA:          “You’re better off using ‘methylene chloride.’  It’s better for the environment.”


S:             “Is NMR-chloroform a halogen?”

TA:          “What do you think?”

S:             “I think it’s halogenated…no, wait, it’s non-halogenated.”

TA:          “Why?”

S:             “Didn’t you say ‘H’ is replaced by a ‘D’ or something?”


S:             “I have a question.”

TA:          “Okay.”  

S:             The student holds up a flask with a boiling stick in it, waiting for an answer.  “What should I do?” 

TA:          “Yes.”  He walks away.  The TA makes his way around the room and returns to the student 20 minutes later.

S:             “Should I add the hydrochloric acid or the sodium stuff?”

TA:          “Yes.”

S:             Sigh.  “That’s not helping.”

TA:          “True?”

S:             Sigh.

TA:          “Oh, wait, you wanted me to say ‘no.’”


  1. [TA:“No, I don’t care if you do the lab or not. But you have to do the lab to get an A.”

    S:“That’s not fair.”]

    classic and all too frequent in its various forms.

  2. I find it’s usually followed by, “I need all A’s for medical school” or “but, I need to study for the MCAT” or even “you don’t use organic chemistry as a medical resident.”

  3. Who ever said the phrase “there is no such thing as a stupid question” was retarded.

    That said, I used it one time, but it was in jest. I said “Is there any question, and remember there is no such thing as a stupid question?”, but it was only as a setup. Then somebody raised their hand and I said “yes you the retard in the back with the stupid question”. Everybody laughed. I of course then said I was joking and apologized, etc. It was a good question though.

    I got in trouble for that one…

  4. Many years ago (and I mean many) when I was a TA, I had one student who drove me nuts by trying to taste every chemical we were using. He and I both survived, but I had to keep an eye on him for a full year. Did any of you have anyone similar? Later, as a neurologist I ran across something called the Kluver Bucy syndrome which he (partially) fit.

    • No. That is indeed weird. I did have students though that weighed out KOH and then transported it back to their reaction in the palm of their hand.

      • Priceless!

        I can see it now:
        S: “My hand is red and burning.”
        TA: “That’s God telling you to drop the course.”

  5. Oh and we always answer stupid questions with “If you can read you’ve got a clear advantage.”

  6. around the corner and down the hall says:

    retread, I don’t think I have ever had a student that would taste the chemicals, but I did have a student that though it was a good idea to snort the caffeine that he had just isolated (using DCM) from coffee. He is lucky that I didn’t see him do it, otherwise I probably would have kicked him out of class…

  7. I’m teaching organic lab as I write this.. This is their first real lab and of course I get the typical first question.

    They need to use 300mg of cyclohexanol (liquid) and every time I teach this lab I get the “how do I weigh out a liquid” question

    • Wow.

      Being an undergrad still, I can honestly say I haven’t done any of that. I get good grades in lab and lecture, but to be honest, I see very little linking the two.

      My fellow classmates complain that it’s the most frequent source of frustration and mistakes. More often than not I’m helping the person next to me and telling them, “Forget the lecture, this is lab.”

      I don’t know, maybe it’s just my university, or maybe I’m failing to conceptualize the link.

  8. I double post between Chemistry Blog and my other, personal blog. This gem was placed as a comment from my personal blog (courtesy of Javaslinger):

    “And this is why I love being a TA. Endless opportunities to hone my sarcasm to a razors edge… :)”

    After a lengthy lecture about safety using conc. sulfuric acid, I had a girl walk across the room with a Pasteur pipette full of it, stop, talk to her friend, spill a few drops on her sneaker, than asked me, “is it bad if I dropped acid on my shoe.”

    Oh, and chemical engineers are notorious for putting hot sand in the trash with their acetone-soaked paper towels. A friend of mine had a fire start in his teaching lab that way.
    S: “What should I do?”
    TA: “Answer this question: what’s your major?”
    S: “Chem E.”
    TA: “Okay, carry on.”

  9. The following actually happened. Just before leaving grad school and entering med school I made some money as a TA in a 6 (or 8) week summer course in organic chemistry cramming a year’s worth into that tiny space (and into fairly tiny brains given what was taking the course). Some had previously flunked organic, others needed to pass it to get into medical school.

    One loathsome twerp had actually been accepted and was to matriculate in the fall (like me) but only if he passed the course. You know the type, every point taken off was fought over, etc. etc. I was pretty sure he was also cheating in the lab. The denouement came with the benzoin condensation. We were shooting for a 70% yield, and sure enough starting with 5 grams of benzaldehyde he got 7.5 grams of benzoin.

    I wanted him thrown out of the course. He was not. God only knows what damage he caused as an M. D. As an older and wiser Doc once said to me — medicine is a licence to steal — the only protection the public has is a doctor who is a little too busy, so that all he does is what he should do, not what he can do.

  10. There are certain Universities that seemingly require an act of Congress to stick a plagerism/honor code offense, and the result is most often akin to a slap on the wrist (taking a 0% on the assignment). Having a sitdown with the Dean is troubling, inconvenient and often pointless because after the meeting, he/she will meet with the student and as, “did you cheat.” When the student says, “no,” without conclusive evidence (amounting to video surveilance), the issue is thrown out.

    Most profs are afraid of approaching students because they don’t want a lawsuit for slander or libel.

    • Yes, but in the case of the benzoin condensation, the twit had actually created matter (see above). About as good as the evidence for cheating ever gets.

    • All too true, but here are a few examples of what I’ve seen in medical practice

      #1 A drug addicted urologist who passed his urine tests (for a while) after he was initially caught by catheterizing his patients, obtaining their urine, then catheterizing himself and instilling their (presumably) drugfree urine into his bladder.

      #2 — The Plaintiff’s friend — a neurologist who didn’t have an examining table in his office and who examined people in their attorney’s office.

      #3 The crooked neurologist, who, to make money, diagnosed hapless neurotics as having multiple sclerosis, plunked them in the hospital and gave them unnecessary treatment with high dose corticosteroids. One of them developed bilateral aseptic necrosis of the hips as a result. Multiple (billable) expensive tests (EEGs, Evoked responses, EMGs, NCVs) were performed on them — it’s called acute remunerative neurology. Fortunately he has now lost his medical license — for incompetence, but it most likely wasn’t incompetence, it was fraud (as we all suspected but could not prove).

      Where do you come in? If you find such an individual throw them out of the course. Would you want them taking care of your mother in a few years? Also if someone says “If I don’t pass organic, I won’t get into medical school” — think to yourself — “If you can’t pass organic, you don’t BELONG in medical school” and act accordingly. It may not be easy, and I have no idea what the academic/legal environment is these days, but you’ll be doing society a favor.

      • I’m off to what a friend calls ‘band camp for adults’ for the next two weeks. Most of the commenters on this blog appear to be on the front lines of undergraduate teaching. Hopefully you guys will produce some comments about your own experiences with the devious, and more hopefully you will help weed out the morally and mentally challenged in your work with premeds.

        I’m sure the way such things are handled has changed (even more hopefully) for the better, but I have no idea what the current situation is. The event described in the post of 7/15/08 occurred over 40 years ago, those in the post of 8/7/08 were much more recent (the crooked neurologist only lost his license a few years ago). I’ll respond when I get back.

  11. During my first semester of organic chemistry for chem majors, someone decided that it was a good idea to buy/sell lab reports on the LiveJournal community. Little did she know that there are a ton of grad students on the intertubes, too.

    My professor found out and was furious. We ended up handwriting our reports for the rest of the semester. Graphs, tables, everything. I was so upset that I actually spent a whole night and figured out her identity. Luckily, it’s not someone that I know of.

    Let me just explain that, the lab this student was trying to cheat on was titled “solubility investigation.” Sigh.

  12. while i do hate stupid questions (and have gotten quite a few over the course of my TA-ships) i’ve always lived with the mantra that ‘a stupid question is easier to deal with than a stupid mistake.’

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