Organic Chemistry Study Tips

By James Ashenhurst

“Make All The Necessary Mistakes As Quickly As Possible”

Last updated: September 12th, 2022 |

The beginning of a new semester is a quiet time. Time to resolve to do things differently. Try and fix problems from last semester to improve them for the next.

One common painful experience is to get exam results back and realize that you understood the material but got a poorer grade than you expected due to the accumulation of a lot of tiny mistakes. This can easily make the difference between an A and a B, or worse.

Ian Gould talks about this in his (amazing) website. He says that one of the most common problems that students have is that:

A student comes to me saying “I understand that I need to practice lots of problems, and I do all of the problem sets, but I keep missing points on the test, why is this?” They are understandably frustrated (again!)…. The mistake the student then makes is that they say “I understand that small problem, I can do these”. What they should be saying instead is “AAAAARGH!! I MADE A SMALL MISTAKE AGAIN! I WILL MAKE THAT SAME SMALL MISTAKE ON THE TEST AND LOSE POINTS!” while pulling at their hair and banging their head against the wall! Once you have learned that doing problems helps, you next have to take it to the next level and aim for eliminating ALL ERRORS. Don’t be tempted to say “Oh yeah, I can do these”, the tests prove that you can’t at least not to your satisfaction! At this point I say to the student. “what is your LEAST favorite color?” Then, “find a large card in that color, and write on it in large letters “I MUST ELIMINATE THE SMALL ERRORS TO DO WELL IN ORGANIC”. Put that card on your desk every time you study organic chemistry.

You have to be pissed off enough about your mistakes to do something about it.

So if you’re beginning Org 2, this is a perfect opportunity to go over your tests and exams from the previous semester and try to objectively catalogue your errors.  One thing that will help is to make a list of ALL the mistakes you made and keep it somewhere. Yes – all of them – however silly they may seem to you now. If you name a mistake, and write it down, you own it.

Everyone – everyone –  who has taken organic chemistry has done things like this:

  • drawn 5 bonds to carbon
  • flipped R/S stereochemistry when trying to draw a molecule in a different configuration
  • drawn the “enantiomer” of a meso compound
  • forgotten a reagent, like adding NaOH to the oxidation step of a hydroboration
  • been at a loss when confronted with an acronym  – like NBS or PCC

There are more: if you want to learn from the mistakes of others, see this handout by Dr. Eric Kantorowski at CalPoly on the Top 20 All-Time Mistakes in Organic Chemistry.

We aren’t born knowing this stuff. Getting things wrong is inevitable, especially in a subject like organic chemistry, where there’s such a huge variety of ways to do so.  But if you keep a private list of the mistakes you do make, and review it regularly, there’s a much smaller chance you’ll make those mistakes again.  This list will come in handy when it comes time to write  your final. You’ll also be able to track your progress.

Try to be a connoisseur of your own mistakes.  I keep a private website where I try to keep track of things I screw up. [Google Sites is a pretty convenient tool for doing something like this.] The other day came a big one. A helpful reader  made me aware that a picture on a post I wrote had an inaccuracy on it, and it also happened to make it into a national magazine that is read by over 100,000 members. Crap. Added that to the list.

Although I can’t find a source for the exact quote right now, John Wheeler, one of the great physicists of the 20th century (Richard Fenyman’s Ph.D. advisor) wrote in his biography that the key thing is not to avoid mistakes, but to  “make all the necessary mistakes as quickly as possible”.

Our knowledge builds on the skeletons of our mistakes, just like the skeletons of millions of single-celled organisms in time build up into a coral reef that rises from the ocean floor.  That is to say, if you’re not making mistakes, you’re not learning.

The trick is to try to make new ones.

By the way, this is yet another reason why doing problems is helpful. It lets you make mistakes in a controlled environment. Then you give yourself time to take action to correct them – before the exam comes up.




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