“America’s Top TA” Shares His Secrets For Teaching O-Chem

by James

in Organic Chem Study Tips, Teaching

[image photo credit: www.nyapplecountry.com]

What does it take to be a great organic chemistry TA?

A few weeks ago, Dan Coiro, a graduate of Rutgers University, was awarded the title of “America’s Top TA” in an online contest sponsored by the learning company CengageBrain. This article in NJ.com should give you an idea why:

 In his first week as a teaching assistant in Rutgers University’s notoriously difficult organic chemistry course, four students came to Dan Coiro for extra help.

Then, word began to spread: Though he was only a senior, Coiro was a teaching assistant who knew his stuff.

Soon, more than 150 students were packing Coiro’s weekly “Rogue Review Sessions” on the New Brunswick-Piscataway campus. In addition, he was fielding more than 700 e-mails a week from desperate students with organic chemistry questions. Dozens more were calling his cell phone in the middle of the night looking for help.

“It started getting somewhat crazy,” said Coiro, 22, of Roxbury. “Once I started doing this, I realized I really love teaching.”

I invited Dan to come on here to share his experiences so we could learn from his techniques for teaching (and studying) organic chemistry. Take it away, Dan!


As far as advice is concerned, I would love to share some of the greatest successes I had in the classroom to help professors relate with their students and help their classroom.

Having received so much feedback from my students I was able to tailor the classroom to their responses. The regular thank you was voiced with some form of the phrase, “Before I met you, I never really knew how to study”. Simply, half of the failing students began to pass as soon as they began to tweek their study habits.

Little pieces of study advice from the get-go were simple;

Use PEN.

The reason behind this is, when a student is given an eraser it can be used as a crutch for mistakes. Instead of scribbling away at a page with a pencil ultimately to be erased, a pen can be controlled to prevent error. If an idea hasn’t been thought through properly, then it shouldn’t be written down. This is a great tool I wish I learned earlier in life to help control the transmission of the thoughts inside my head to paper.

After some positive feedback about using pen from students, I thought about this further and the concept of thinking about the material critically with poise instead of fumbling through scribbles and errors. What if all that is needed to do well is for students to mentally digest material before they even begin to write it down? My philosophy is that the best teacher in the room is always the student because each person has a different style of learning. Real learning happens when a student figures out their own study method that works for them and not everyone else’s. What better way other than trial and error! Obviously, Some learn things more quickly than others in certain subjects; I still don’t get abstract algebra… Indeed I offered my study advice to students when they asked for it, but my job was to instruct chemistry concepts and to get students to think about thinking, not to get them to memorize a bunch of stuff that they may not even be interested in pursuing in the future.

So, I started experimenting with my own teaching ideas and my students thankfully went along. As far as organic chemistry is concerned, my teaching style culminated to the following:

Teach a concept and pieces of other material that coincided while making sure to highlight newly acquired vocabulary terms with old ones to get constant reinforcement of their foundations( E.g. “In this case the ‘enolate’ is experiencing inductive withdrawal from adjacent fluorines… What can we say about this species nucleophilicity?”). We can agree that constant exposure to the language is key to really understanding organic chemistry.  Every chemist uses jargon, I mean will never use the IUPAC name for acac. Each concept was said 50 different ways in attempt to get everyone to understand. I tried to make jokes when I could, “A nucleophile is like a pedophile that looks for either positive charges or delta charged atoms because they are ‘exposed’.” Although it was slightly inappropriate, no one in the room forgot what a nucleophile was throughout the course.

The thing that worked the most was that I demanded during those 20 minute or so intervals, students didn’t write anything down. I did. I wrote down only what was necessary on the board, no bull. The things that were on the board were key words and buzz words, things that tooted a horn to remember the concept. Of course, there was also reactions and diagrams that I used to deepen their understanding.

Once the board was full after about 20 minutes or so, I had them write the info down while answering questions about that segment. If they didn’t get it, we didn’t move on. For me, that meant another after hours review session, but it was worth it to see them understand.

During the whole review, I threw problems on the board that tested understanding of the concepts. I always ended with a synthesis problem that incorporated the every reaction that they were learning in the session (Obviously prefabricated before hand with diabolical intentions to get them to think about it for a week or so). Their job was to figure it out and get the solution to me by the following week including the mechanisms that went between reactions. The exercise helped their mechanism work tremendously. One of the reasons why this was so successful was because it made it easier to remember reactions by putting it in a sequence rather than a jumble of transformations with no end game.

I always made the reactions a part of a synthesis of an important small molecule seen in medication, ie. aspirin, propofol, epinephrine, etc. Things that people can attach a story to. “If you don’t pass this class, at least you can go make meth to pay off your student debt…” No harm no foul in making fun of Michael Jackson Juice to get them to remember alkylations, protecting groups and diazonium salts.

I cannot say that this method got everyone an A in the class, but they all passed and enjoyed themselves.

So, as for how this can help your website? I am not entirely certain. All I can say from the small amount of experience in the classroom that I have had is to adapt to what works and scrap what doesn’t, both on the end of student and teacher.


Awesome job, Dan. I can guarantee you that I wasn’t giving out my cellphone number to my students when I was an organic chemistry TA – my focus was on my Ph.D. research. The dedication, time, and energy demonstrated here is truly impressive. Congratulations on an award well deserved

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Congrats, Dan — best wishes in your career goals, too!


Med School Odyssey

Interesting view. My undergraduate adviser spent hours breaking of the very habit you tried to instill in your students. I found when writing proofs or solving problems that I often didn’t want to write anything down unless I could see my way to the end of the problem. Unfortunately, most graduate level science problems in math or physics simply can’t be done that way – no one is able to see their way to the end of the problem until they are working on it. Solutions take time to form and without trying and failing, you never get anywhere. I found that problems which initially seemed intractable became possible, once I started writing down the beginnings of a proof or a solution and, even if I had to erase or start over, eventually I’d be able to figure it out.



I have found that erasing a mistake in a synthesis or retro-synthetic analysis does just that; it erases the thought process which led to the mistake. I purchased a whiteboard and began to work out reactions there, and rather than erase my mistakes I’ve taken to just marking them out in a different color, say red, then rewriting the problem backward and forward the correct way once finished on paper. This way I can still see what I was doing wrong the first time in order to get to the root of the problem and avoid the same mistake in the future. I go back over the material/notes to determine the reason for my initial misunderstanding of the mechanism which leads me to a deeper understanding of it. In turn, I am better able to apply the concepts to any related reactions. And of course the concept is only half of the battle. I still make flash cards with starting material and product on the front and reagents are listed on the back, and either starting material or product with reagents and the mechanism and result of either synthesis or retrosynthetic analysis on the back. But the whiteboard has been my best friend, and has saved a lot of trees.


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