My Organic Chemistry Story – What’s Yours?

Late one Friday night in building 18 at MIT a few years ago I synthesized a molecule called dideoxyverticillin. It looks like this.

It’s part of a family of molecules that had evaded synthesis for over 40 years and required solving some particularly tough synthetic problems.  Our work was published in Science, arguably the world’s most prestigious scientific journal, and the synthesis was covered in chemical news sites like C&E News, Totally Synthetic, and even given its own chapter in the book, “Classics In Total Synthesis III “.

You might think that in order to be part of an achievement like this, I must have been an organic chemistry prodigy, born with the ability to memorize reactions with ease,  do synthesis in my sleep, and draw perfect hexagons from the age of 4.

That’s far from accurate. Actually, my grade in sophomore organic chemistry was 68 – a C+ in the Canadian system.

In other words, mediocre. Class-average.

And it’s not like I slacked off. From the moment I knew I would have to take organic chemistry,  I was excited to learn about it and determined to do well in my class. I was aware of its reputation for being difficult so I decided I would work as hard as I could to succeed.

Here’s some of the work I put into the class:

• worked through five chapters worth of problems the summer before taking organic chemistry
• Went to class regularly, sitting at the front (which I never did)
• went through the professors’ recommended list of practice problems
• had a solid 7 days to study for the final and spent it studying and doing problems, as well as making comprehensive flashcards.

I never had as much concentrated time to prepare for an exam. And I don’t recall a single class from my undergraduate career where I had wanted to do well as badly as in introductory organic chemistry.

And despite all of this – I still got a C! 

I desperately needed a result in the 80’s to bring my mark up to the low B-range, but instead I got something like a 64. I went to the instructors office after we got our exams back, on the verge of tears, wondering where I went wrong. In the pressure of the exam, I missed things like seeing that CH2O can be used as a “reagent” to form acetals, for example.

Here’s the unfortunate lesson I took away from my experience in organic:

No matter how hard I try in organic, I’m bound to fail. I’m not smart enough to do organic chemistry. Other people smarter than me were lucky enough to be born with the ability to do organic, but not me. 

And for years, I believed that. It’s a long story, but eventually, I realized that organic chemistry was the intellectual love of my life, and came back to it.

Unfortunately, many take the same lesson from organic chemistry as I initially did, and it scars them in some way. To this day sometimes when I tell people I’m an organic chemist they say, “ugh, I [frickin’] hated that class!”.

Here’s some lessons I wish I had taken away from my organic chemistry experience instead.

Tactical

• Focus less on memorizing long sequences of arrows, and chunk mechanisms into steps – like this. Look deeply for recurring patterns: “nucleophile attacks electrophile” is the key pattern of almost every reaction in organic chemistry. Understand which parts of molecules are electron rich, and which are electron poor.
• I probably worked alone too much. Don’t be too proud to strike up conversations with strangers in your class to find people – at your level, hopefully – to study with.
• After doing a practice problem, I should have asked myself what I learned from it, instead of just mentally ticking it off and moving on to the next one.
• I should have kept a journal of mistakes that I made and reviewed it regularly.

Conceptual 

• College is a kind of  tournament. My class was a tournament. Of course my instructors job was to teach, but he also expected to produce a roughly bell-shaped distribution of grades at the end of the semester. Sadly, it was not always in his interest to point out common points where students trip up, because these could be prime trick-question material.
• This means: my grade is not my intelligence, my grade reflects my exam performance in the tournament.  I was far too hard on myself thinking I was “dumb” for not doing better in organic.
• Some instructors design the “tournament” in different ways. Some courses test at a highly conceptual level, requiring you to apply key concepts.  Others have long lists of reactions with blank “product” boxes. This is why you have one group of people telling you “don’t memorize, learn the concepts”, and another saying, “it’s all memorization”.
• Organic chemistry isn’t like math, where a genius like Ramanujan can logically deduce a great deal from a given set of principles. Which is not to say it’s illogical –  it’s just that there are many variables in play, sometimes acting in opposite directions, and it’s hard to predict which of these variables will dominate in different situations. Organic chemistry is an empirical discipline, where knowledge is hard-won by experiment. Markovnikov may have made the observation about addition of HX to alkenes, but he didn’t predict it in advance nor did he understand exactly why alkene addition reactions happen that way. It only looks obvious in retrospect.
•  If you find yourself mystified by certain reactions and reagents,  that is a perfectly reasonable response. Instructors (and textbooks) have a bad habit of presenting certain new reagents and reactions like they are obvious logical extensions of concepts explored previously and don’t convey the depth of experimentation and failure that went into their development. It’s possible to cover the Sharpless epoxidation in 15 minutes of lecture, but that doesn’t convey the dozens of man-years  of experimentation that went into its development. Introductory courses don’t give you the full story.
• Organic chemistry is so incredibly deep that a two semester course doesn’t do it justice. Instructors are under pressure to cover a lot of material in 12 weeks of lecture (24 for Org 1 + 2), and a lot of the important conceptual underpinnings that would help students to understand the material more deeply are poorly developed.

I could go on about how I am still bitter that my instructor didn’t do a better job of explaining some of these latter concepts but I don’t want to belabour the point. I will say that part of the reason I started MOC was in the hope that I could reach people who are struggling with organic chemistry and help coach them through the course in a way I never was, and maybe help them avoid the wasted years of feeling “dumb” that I experienced.

What’s your organic chemistry story?

What have you learned from taking organic chemistry?

Reply in the comments.