Organic Chemistry is a Paper Tiger

Well, there are two weeks of class left before the final examination.  I went into this course with a bit of trepidation after hearing all the horror stories and, now that I’ve pretty much reached the end of the tunnel, have concluded that the difficulty of organic chemistry is far overstated.  He’s never given us a grading scale, so I didn’t really find out until after the last exam where I stood, though I was pretty sure I was in good shape.  The average on our last exam was a 45% and I got a 77%, which was one of the top scores – I think the highest was an 81%.

The point of this post isn’t to boast about my grades or ranking in the course – both are fine and my professor told me that I don’t need to worry about my final grade.  Although, if I stopped turning in homework or didn’t take the final, I’d imagine that would change.  Anyway, I’m not too worried about the course at this point, which is a nice feeling.

Someone asked a while ago for me to post some things about learning organic chemistry that I found frustrating.  Here they are in no particular order:

  • Textbooks are great at giving simple examples of a particular reaction mechanism – the paradigm reactions are easy enough to understand.  What infuriates me, however, is when the text (or lecture notes) show the mechanism for a very simple reaction, and then show reactants and products for a much more complicated reaction, without showing the mechanism.  If instructors are trying to emphasize understanding, it would be much more useful to actually show what’s happening and why, rather than just showing the reactants and products and leaving the rest up to the imagination.
  • How many times have you heard “the molecule is happier with the positive charge here rather than there”?  This annoys me to no end – stop trying to simplify things by anthropomorphizing.  Charge at one location is preferred over another for good reason, most of which are fairly well understood.  Students are old enough to hear about things like charge stability and lowest energy states.  Imparting emotions to a molecule or atom just makes it more difficult for students that want to understand what is actually going on.
  • I’m a big believer in learning objectives for science courses.  Textbooks typically cover an enormous amount of information, much of which isn’t going to be covered in the class and can be safely omitted when the student is reading before and after lecture.  My experience this semester would have been a lot better if I had known specifically what it was that we were expected to know after we had completed a particular section.  This would have made studying much more targeted and helped me to fill in holes at the end of the section, rather than wasting a lot of time trying to figure out which subjects were important and which weren’t.

Here are a few things I’ve learned about this subject that students ought to be aware of before they take this class.  I doubt any of these will be new for most people, but hopefully, others can benefit a bit from them:

  • Success in organic chemistry can be helped or hindered by the quality of your professor and classmates.
  • Study groups are not the necessity that everyone says they are.  While your mileage may vary, study groups are often an enormous waste of time.  I met about once a week with 4 other people to review our answers to the homework and review problem subjects.  After the first exam others realized we knew what we were talking about, so we wound up with about a half dozen party crashers when we got together, all asking us to teach them organic chemistry.  Bottom line – if you have a study group, get together to go over what you’ve already done outside of class and don’t invite people that will distract you from that goal.  A couple hours a week is probably sufficient for this.
  • The reliance upon memorization as the key to success in organic chemistry is a mirage.  I don’t know what you would actually memorize – I haven’t seen anything in the course that I felt could be memorized, so if you find yourself making flashcards, you’re doing something very wrong.  Maybe for learning functional groups you could do this, but you’re going to use them enough that you’ll have them wired after a few weeks anyway.
  • Do some problems or reading every day.  I didn’t do this because organic chemistry isn’t all that hard for me to get a handle on, but if I had, I’d probably understand things better than I do.  I’ll probably spend a good chunk of winter break reviewing a few key chapters to get a handle on things better.
  • Don’t let yourself get psyched out by the people around you whining about how difficult organic chemistry is.  I let myself get taken in by the horror stories around the first exam and did substantially worse on the first exam than I should have simply because I bought into the idea that it was tough and I was going to fail.  I learned a lot more about myself and self-confidence during the first few weeks than I did about chemistry.  If you’re surrounded by negative and pessimistic people, tell them to piss off – don’t get sucked into their game.  Prepare and study well – play your game, not theirs.

Best of luck to everyone that’s taking organic chemistry now or in the future – I’ll post some updates on the course over the break.  Happy Thanksgiving everyone!


4 Responses

  1. Great post.

    Let me add a few points:
    1) re: the mechanisms I would *love* it if you could give me a specific example (or two) of what you’re talking about – write me at . This would really help me teach.
    2)Part of the challenge of putting a course together is being able to reach as many people as possible, who have diverse learning styles. Some people have trouble with abstract concepts than others, or learn through analogy. Anthropomorphizing is done so as to reach the many people in the class who are totally lost and have trouble with abstract concepts. You’re at the tail end of the best students in the class from the sounds of it. There are many different learning styles. If your prof was teaching you one-on-one, he/she probably wouldn’t do it.
    3) I agree that a list of skills/goals for the course is an absolute necessity for personal evaluation. This needs to be done *much* more. Otherwise you don’t know the destination of your journey, or how to recognize when you have arrived.

    4) I have seen students change their attitude 180 degrees upon getting a new organic chemistry professor, both directions. It does make a huge difference.
    5) Learning groups obey Gresham’s law. If you can find just *one* great person you can study with, that’s all you really need.
    6) “Play your game, not theirs” – well said.

    Congratulations on your standing and good luck for your final.

    • Thanks for the comments – you’re spot on. My study group is pretty much the top 5 students in the class. We’ve all consistently had the highest homework, quiz, and exam scores. I find it interesting that we’re all older students, ranging from 26 to 33 and I wonder if there’s a causal relationship between the age and success in the course.

      About the mechanisms, I’ll give an example here so that those following this blog can understand what I’m talking about and I’ll send you an email later with some more information so we can have a bit of dialogue about it. A good example of what I was referring to involves an elimination reaction. The archetypical reaction to illustrate E2 reactions is something like a hydroxide ion attacking tert-butyl bromide. It’s simple enough to see how substitution is difficult with all the steric hindrance present, so deprotonation of one of the methyl groups makes sense and you can work out the rest pretty easily, because the reaction is rather straightforward. In the next paragraph, the textbook shows a reaction between 2-bromooctane and DBU at 90 deg C without a solvent to produce a 4:1 ratio of 2-octene and 1-octene without any discussion as to how it occurred. I quote “The following transformation illustrates this result for the E2 reaction of…”

      That’s the sort of thing I’m talking about. Introducing the mechanism with a simple reaction and then jumping to a more complicated reaction and not showing the mechanism at all had very little illustrative value for me. More and more organic chemistry professors seem to be waking up to the need to focus on mechanism. But, unless the textbook actually makes this a priority, it’s difficult for me to see how it can be of any use to the student.

      And on the anthropomorphizing of physical properties, I’m still not certain I see the benefit, though I’m sure there is some utility to it. At some point, science students (whether they be future chemists, physicists, engineers, or physicians) need to develop the sophistication to understand things like thermodynamics. If they aren’t going to develop it in organic chemistry, when will they? I also tend to think that it makes things more difficult – wouldn’t it make things easier for students if they were introduced to some of those concepts early on in the course, rather than spending a year trying to memorize the conditions that make molecules happy?

      Oh, one final thought on organic chemistry preparation – after watching students flounder in this course and hear the questions that they have, I’m convinced that organic chemistry would have been a lot easier for them if they had taken the physics sequence prior to taking the class, particularly one which incorporated some modern physical concepts as well (solutions to the Schrodinger equation for the hydrogen atom, statistical mechanics, and some basic QM concepts, including spin).

      Personally, I’ve loved organic chemistry, but that was probably because I had a much larger background than most of my classmates did. I was explaining to a classmate the other day why a reaction had two different products at different temperatures and, in order to do that, wound up needing to explain the relationship between energy and temperature and then work through Boltzmann distribution. It seems to me that organic chemistry would be a lot more straightforward and make a lot more sense if students had at least been introduced to these topics prior to the class. What I find really shocking is how I heard all the horror stories about organic chemistry, but the one subject I hear people whine and complain about the most is physics.

  2. […] How to Do Well in Organic Chemistry: One Student’s Advice Posted on January 17, 2011 by James Over at Med School Odyssey, the author recently wrote about finishing Org 1, and has a lot to share about his experiences with the course. Here are some choice excerpts from that post, and from a few of his earlier posts. […]

  3. Hmm, I get where you’re coming from, Med School Odyssey, but I’m sorry to say I don’t entirely see “eye-to-eye” with some of your points:

    1. My textbook, at least, covered all the important mechanisms for the course, and my instructor put strong emphasis on learning the mechanisms by covering a lot of example mechanisms in class, especially the harder ones. It was my first organic chemistry professor who taught me the importance of mechanics, stating that we had to learn them, or else suffer through misery of memorizing hundreds of reactions.

    2. I think the whole anthropomorphizing thing is done to make the material less dry, more down-to-earth, and more exciting. Although my organic chemistry professor didn’t do it at all, I like it because it’s amusing and shows that the professor has a sense of humor. And as Einstein once said, “Any intelligent fool can make things bigger, more complex, and more violent. It takes a touch of genius — and a lot of courage — to move in the opposite direction.” Making things simpler ensures that a lot more students will get the most basic concepts so that if and when they take more advanced courses that build upon chemistry principles, they have a solid foundation; or, they could, of course, teach themselves the details and complexities of the concepts, which should be easy as pie after getting the gist of it. Obviously, anthropomorphizing isn’t the only way to simplify the material, but I believe it is effective enough that it is still a respectable way of teaching.

    3. I guess I have a really good textbook and professor then because my textbook highlights the key points at the end of each chapter, and my professor spells out in the syllabus the fundamental topics in the course. Also, we cover the entire textbook over the 2-semester course, so my textbook is probably a lot more concise. Study aids like Organic Chemistry as a Second Language are really helpful for pinpointing the important topics to know for the course.

    Do your classmates really whine that much about how hard organic chemistry is? It’s always been the opposite for me–my classmates were talking about how organic chemistry was a piece of cake, just a time-suck.

    I find it helpful to hear about how difficult a course is from other people, even if it just turns out to be hype because instead of getting scared and unconfident, it actually only makes me more determined and excited about that course. Instead of “whining” to people that organic chemistry is difficult, if they ask me how it is, I tell them that it’s difficult, but not as bad as people say it is so long as you do problems daily and don’t get behind. That way, they don’t make the mistake of underestimating it like I did, nor do they worry about it excessively.

    In the first month of organic chemistry, I found the class to be ridiculously easy because it was just a re-hash of general chemistry concepts, like bonding, electron energies, molecular structure, acids & bases, resonance, etc. Since I hadn’t heard of organic chemistry being that scary, I figured I could coast through the rest of the course without too much trouble. And then, there was a massive difficulty spike for me when we started covering molecular orbital theory, with a bit of basic quantum mechanics principles.

    I spent hours and hours trying to understand the concepts in order to do the problems, but this only caused me to get behind in the course, resulting in a very miserable time the week before finals. I think organic chemistry ended up being the first course I’d taken that was not crammable. I was able to get A’s on calculus-based physics exams by cramming the night before, but that didn’t work at all for organic chemistry. For me, the hardest thing about organic chemistry was time management–parceling out chunks of time every day instead of spending 15 hours on the weekend. The rest of the first semester, as well as the second semester, has been quite challenging for me, despite my having a very strong chemistry, physics, and thermodynamics background. Still, the material has been quite manageable compared to the challenge of time management.

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