Common Student Difficulties in Organic Chemistry

While cleaning out my newly assigned “war room” (the setting where I’ll strategize on how best to torture students this fall), I came across some fairly interesting documents that were buried in far corners of crowded file cabinets.  They’re nothing personal or discriminating (sorry TMZ), but I saw them as material I could use in upcoming classes.

One of the several I found, titled “Common Student Difficulties in Organic Chemistry,” caught my attention more than the others.  The document, which appears to have been assembled using a typewriter (for the unfamiliar, you can find information about typewriters here), lists problems students encounter while navigating through the dreaded “O Chem”.  In any case, at the bottom of the page, in bold, is the following message:

If you start to get into trouble in this course review this sheet.  Knowing what has gone wrong allows you to fix it.

This closing interested me from a historical perspective.  Did enough students bomb the course to warrant this document’s assembly?  Did the professor discover this or a similar list at an ACS meeting and felt it was prudent to include it in his/her course?  Did the document actually help students better understand the course material?

Although I can speculate until the cows come home, I’m throwing it out to you, the blogosphere.  Do you agree with this list?  Would you change anything on it?  I’m curious to see what the blogger generation thinks (FYI, I believe this list was developed in the 1980’s).

  1. Lack of organization
  2. Difficulty in keeping up with lecture while taking notes
  3. Failure to finish exams
  4. Inability to manipulate three-dimensional structures on paper
  5. Too little drill – lack of repetitive practice
  6. Falling behind
  7. Poor problem analysis
  8. Inability to see and mentally manipulate three-dimensional objects
  9. Insufficient energy and/or motivation for the challenges of this course


  1. An inherent inability to mentally manipulate and transcribe 3D objects will separate the As from the A-s, but I don’t think it is a critical detriment.

    • It depends on the field. I can work with two dimensions on a *good* day…I’m fine in flatland, but I don’t do well with natural product structures or anything similar.

  2. Bryan Rowsell says:

    I find that recognizing bond dipoles is a skill they never fully acquire in general (I teach both general and organic). For me, that helps them with arrow pushing.

    I give my students this article a month before the final exam in the first-semester course: Mullins, J.J.,J. Chem. Ed., 2008, 85, 83.

    Are those nine points all that was contained on that document besides the aforementioned warning? I’d be interested to see a scan of it!

  3. When I took over my current teaching position, the previous teacher left behind a lot of useful stuff. I found one folder labeled: “Diabolical problems in Organic Chemistry.”

    From the list, I think 5 and 6 are the big ones. There are too many distractions (i.e. video games) to keep one from studying. Falling behind in O-chem is a death sentence for most.

    • I’m completely confused as to why many professors teach above their students (particularly on the undergraduate level). It’s a huge pet peeve of mine.

      I’ll also agree that distractions can be the difference between pass and fail. Fortunately, I found a small corner of the library just in time ;-)..

      On a completely different subject, do you think I can get away with using Wyeast American Ale 1056 to make a dry Oktoberfest ale? I don’t have the capabilities to lager just yet.

      • Stewie Griffin says:

        I’m sure Papazian would say to use whatever yeast you want, and I agree. It’s your beer so make it your own 🙂
        It’s fun to make your own unique batch, so use the ale yeast and see how it turns out.

        • cookingwithsolvents says:

          After a minimum of ~8-10 years specializing in chemistry (PhD+postdoc) and often many, many more it’s sometimes tough to know where to aim the content level. Plus, one has to keep the pack moving and that includes the top students as well as the bottom. Since the top students are more fun to work with it’s human nature to sometimes teach more to them (or a little above THEM).

          1056 is a good choice but I agree with stewie…just make some beer and tweak it next time (or make something different…I’ve only ever tried to make the same thing twice one time and even then I was tweaking).

  4. My high school chem teacher gave us a type-written copy of “The 10 Commandments of Chemistry” that I use with my students now. I do find that a lot of their mistakes are exactly what I warn them against. From my memory of orgo, that list looks pretty useful.

  5. I’m fairly certain I’m preaching to the choir, but #9 is THE problem. All the others are ancillary to that and stem from a lack of motivation/discipline.

    I recently read a ratemyprofessor review from my grad school and one of the o. chem profs was recommended because only the barest minimum amount of work was necessary to pass.

    • Motivation is horribly difficult to control.

      • It’s impossible for you as the professor to control it, it’s entirely up to the student to ask themselves whether they’re willing to put in the work necessary to get through. Is it really your dream to go to medical school or is it your parents’ dream and they just hammered it into your head for so long that you believe it’s your dream? Finding that internal truth is the key to finding your motivation.

  6. I don’t see how this will help students improve – it basically says “work more.” They all should know that by working harder all 9 of these issues could be alleviated. If this list really wanted to be helpful to students it should be more specific.

    • I understand what you’re saying, but it’s the same approach organic professors have been saying for years. I like the list because it takes an alternate approach toward reaching students than the explicitly saying, “work harder.”

      • Most of the time orgo difficulty probably is the student’s fault, but the list sort of seems to absolve the professor of any responsibility (if you suck, it’s because you’re not working hard enough). One of my professors (that I liked) tossed fastballs over the class’s heads on a regular basis – the problems were neat, but even for advanced orgo, they were a little steep. One professor didn’t really seem to care – I know you can’t make students care and so not professors either, but that was his job. Sometimes, teachers may not have gone through the material enough to organize it coherently in a way that helps it to make sense (grad school – prof replacing another prof who was on sabbatical). In any case, there are enough mistakes that profs can make/do that absolving profs of all responsibility for conveying the material seems unjust.

        azmanam’s list seems like a better idea. If you can lower the activitation energy to studying (by being able to solve a problem), people will probably do better.

  7. Having just taken O Chem (and fallen behind and caught up enough to get an A-) I would say that a few of those points are very useful, but most are merely being a good student. I was hoping for some more specific advice. I would say that falling behind is one of the worst things you can do, though. Many classes don’t continue building on the previous things like O Chem does. And yes, manipulating 3D objects on paper and in one’s head are very important. Overall one of those lists that, for the most part, make me feel insulted that teachers think I hadn’t thought of having good study strategies until they suggested it.

  8. I like the list (with the exception of #8) as a general list of things to do to make improve in any class. As I’ve been tutoring during my time in grad school, I came up with a list of 6 Truths to keep in mind when running homework problems or on an exam for Organic Chemistry. When I start teaching for real in the fall, I’ll likely share this list with my students:

    #1) Approach unknown reactions just like you should approach all reactions
    – Identify nucleophile(s)
    – Identify electrophile(s)
    – Nucleophiles attack electrophiles
    – Repeat

    #2) Weaker Acid Wins
    – In and acid/base equilibrium, the equilibrium favors the side of the arrow with the weaker acid (the compound with the higher pKa)

    #3) Mind your charges
    – Make sure the net charge of all compounds is consistent throughout a mechanism

    #4) The 2nd Best Rule
    – The 2nd best resonance structure usually defines a functional group’s reactivity

    #5) Carbonyls: THE CODE
    – There are only 3 elementary steps in a carbonyl addition mechanism.
    1) Proton Transfer (always reversible)
    2) Nucleophilic Addition to a Carbonyl (electrons go up onto oxygen)
    3) Electrons Collapse Down from Oxygen (and kick out a good leaving group.
    The steps can be in any order and repeated, but those are the only 3 steps needed for addition to acid chlorides, acid anhydrides, aldehydes, ketones, amides, esters, and carboxylic acids (including aldol and Claisen reactions)

    #6) When in doubt: Number Your Carbons!
    – When coupling 2 molecules, if it not readily obvious where the various atoms go in the product, number the carbon atoms in the starting material and map those numbers on to the product.

    • Thank you for sharing your list.

      I have two comments to make (one of which is symmantics).

      1. I like the “2nd Best Rule.” I think its something all organic chemists do, but don’t ever really stop to think about it.

      2. I once used the phrase “kick out methoxide” when describing a nucleophilic acyl substitution in front of my PI. A five-minute hammering ensued and I now use the word “eliminate” instead.

      • The only symmantic lashing I’ve (we’ve, our research group) ever received has taught us never to call molecules ‘guys’ in a presentation. Now it’s a game to see how many outside speakers per semester call molecules ‘guys.’ The number is startlingly high.

        point taken 🙂

        • Well since we’re nitpicking, your spelling of semantics could use some revision, he he.

          In terms of seminar games, my advisor was notoriously talkative and was known to use certain catch phrases or jokes at EVERY opportunity. We started making bingo sheets of them for seminars and group meetings.

        • It’s so freakin’ hard to decide what to call a multi-functional group molecule. “This here ester thing” is just so cumbersome, sometimes.

      • oh, and yes, I love the 2nd best rule, too. It’s probably the biggest secret to solving organic mechanisms that no one knows about. Maybe I should make a mock magazine cover with the teaser “6 secrets chem profs DON’T want you to know!”

      • cookingwithsolvents says:

        Geez, this reads really curmudgeonly….ah well, it really bothers me sometimes: I hate, no LOATHE the expression ‘I reacted A with B’. No, you allowed them to react, treated A with B, or performed an experiment consisting of the reaction of A with B. YOU did not climb into the flask and swing a big ‘ol A into B resulting in molecular transformation.

        I’ll even take (and use) ‘hit A with B’ or other slangish stuff…

    • I agree with these ideas (teach reaction mechanisms). I think the problem is how to get students to act upon them. I had taken a slightly different approach to getting students to do this. I had planned to discuss, “How well do students understand the curved arrow convention?” at the BCCE (

      I preferred to use example based teaching. For #1, I would rather give a number of examples of the reactions showing bond formation and cleavage. At the end, I would say the group donating electrons in a reaction is a nucleophile, etc. From the examples that students do, they can then classify atoms as nucleophiles and electrophiles. (I think textbooks cover the descriptive aspect. I presume it isn’t a weakness of the descriptions, but likely application of the meaning to actual problems. I think that is where my approach is useful.)

      #2, this is chapter 2 of A Guide to Organic Chemistry Mechanisms.

      #3-6, I do this in class by having students actually solving problems and I walk around the room to check their results. Again, I did this with photocopies of problems from my book. Because problems are broken down into different levels, students can always solve them. I would usually remind individual students of #3 and #6 (yes, the structures are already numbered for rearrangements or Diels-Alder reactions).

  9. Where my students have the most problem is that they never really strive to understand mechanisms or nomenclature. They memorize everything and are surprised when different structures show up on tests.

  10. Pingback: The Six Pillars of Organic Chemistry « Master Organic Chemistry

  11. Pingback: The Six Pillars of Organic Chemistry — Master Organic Chemistry

  12. Hi Jeremy,
    I am a high school chemistry teacher, and each year I see kids fall into the trap of what I call the “snow ball effect”. It is essential to have a plan in place when you decide to take chemistry. Some of the ideas you mentioned (and those that other mentioned that are found within your professor’s compilation) are excellent ways to be successful in chemistry.

    On my own blog, I have created post about how high school students can be successful within my course. The link to my blog is below.

  13. Pingback: Comment Post on Student Blog Regarding How to Be Successful in Chemistry | Ah! The Element of Surprise

  14. Pingback: 2-D-1 How to Be Successful in Chemistry | Ah! The Element of Surprise

  15. Pingback: The Six Pillars of Organic Chemistry — Master Organic Chemistry

  16. I find it interesting that none of these responses postulate that the teacher-student learning environment as a partnership. Many of the 9 items listed could be reframed instructionally; does anyone ask, “Why are my students (insert any phrase from above) and is there something I can do differently?” Walking into a semester with a list of “Why my students fail…” seems like a self-fulfilling prophecy to me. Ask your students–talented Ochem ones and the ones who seem to exhibit any of these 9 “characteristics” what would have helped reverse these effects. Put your ego aside and listen, they’ll tell you. More and more I realize that expertise does not equal all the answers. I would never hand a list like this to my students, unless I was committed to stifling their learning from the get-go. Disappointing and archaic, teaching is more evolved than this.

  17. I whole-heartily agree with this list. Especially the poor analysis bit.

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