Memorizing ‘Don’t Memorize’: The Orgo Oxymoron

In a Reddit thread posted almost a year ago, user “james_ash” asked other users to help define what people mean when they suggest to new orgo students, “don’t memorize, learn the concepts.” Another user named “grimmra2” replied within the thread, “Organic chemistry is like a language. Your instructor wants you to learn it by trying to construct different sentences (i.e. try mechanisms on different molecules), not memorize a conversation verbatim.”

I remember my sophomore year at the University of Notre Dame, I needed to fulfill my language requirement for my Biochemistry major. I had taken Spanish in high school, and college is a time to try something different, right? So, I went with Italian — similar roots to Spanish, yet obviously an entirely different language.

The worst was starting off a phrase in Spanish and seeing my professor’s face start to fall, with that look he’d give me that seemed to say “I know you know better.”

But then I’d catch myself, knowing internally that I was close but had made a mistake, and restart. I had those tools necessary to learn Italian — the pronouns, the vocabulary, the conjugations. I just needed to learn how and when (and when not) to apply them. It wasn’t about memorizing individual phrases, like anyone who has taken a foreign language class before can tell you; it’s about memorizing the words and rules and, yes, the exceptions to the rules to be able to form your own sentences, instead of memorizing sentences straight from the textbook. Otherwise, you’re left with just a handful of stock phrases that won’t get you anywhere.

Thus, I learned one of the most valuable rules of mastering organic chemistry: don’t memorize anything … right?

 

on second thought

On second thought, contrary to what you might hear, you will actually have to memorize a thing or two to succeed in organic chemistry. If you ask any “expert,” they’ll advise you, “don’t memorize; learn the concepts.” And to an extent, that is true — just like how simply learning phrases in a language doesn’t make you fluent, simply learning which set of reagents will add which functional groups doesn’t make you a master of organic chemistry. If there are a number of phrases you can use to express a certain sentiment, then there are a number of reagents you can use to get from a given molecule to your desired product.

That’s where “learning the concepts” come into play. You have to understand the rules of when each reagent is applicable. Just like knowing when to use the formal versus informal greetings in a different language, you have to be able to understand — given certain scenarios surrounding your molecule and reaction conditions — when you can even consider certain reagents.

Furthermore, it’s not always about what you absolutely can or cannot use; sometimes, it’s about what is feasible or what is appropriate when in “realistic” conditions. Once again drawing upon the foreign language parallel, you wouldn’t use more words than is necessary to convey a simple message. Or in another example, you wouldn’t use a flamethrower to light a candle — overkill (and frankly, just dangerous). So, sometimes you would notice how a given set of reagents and reaction conditions will technically get you to the same place as another set of safer reagents with more reasonable reaction conditions. Thus, you need to “learn the concepts” so you can exercise proper judgment as to which reagents to use, and when to use them.

reagent stock

But at the same time, this is where the memorization comes from: you actually do have to memorize some things, otherwise you have no foundation to lay your building blocks of organic chemistry knowledge on.

Let’s go back to grimmra2’s orgo-as-a-foreign-language example: sure you don’t learn a language by simply memorizing a set of phrases verbatim. Instead, you learn these phrases so that you can reverse engineer them and find out how they tick; then, you can learn why you use that certain phrase in that given situation, and why you wouldn’t use it any other time. However, at the end of the day, you do need to know those vocabulary words, those fundamental building blocks to even understand those concepts.

What are some of these building blocks that you do have to memorize? Well, it’s whatever you define them as! There were some pretty obvious ones that my classmates and I needed to memorize: the IPUAC naming system (which you can master as well easily with our Full Year Naming Guide!), what’s an acid and what’s a base, what it means to be oxidized or reduced and how to distinguish between different diastereomers. Then there were some things that I found myself needing to memorize in order to quickly be able to understand concepts and reverse engineer problems to understand their basic concepts — things that maybe some other students didn’t need to memorize and understood intuitively, but I still needed to make flashcards for before moving on to more complex concepts (things also worked vice versa, obviously: there were things that I didn’t need to think twice about that other friends spent a lot of time on).

So at the end of the day, you need to have lay your foundation of organic chemistry knowledge in order to build upon it, and before you know it you’re building up your house of organic chemistry knowledge! (Was that a bit much? Well, my professor also told us that the cornier the example or the mnemonic, the easier it is to remember.)

Thus, I leave you with a quick summary of what it means to “don’t memorize,” and how to use it effectively in order to succeed in organic chemistry.

  1. Forget what they say, actually memorize what you need to. Whatever you need to memorize, do it so that you can work quickly while learning concepts. As you can imagine, it would be hard to watch a movie in a foreign language and constantly refer to the dictionary the entire time to figure out what’s being said; similarly, you can’t always refer to a cheatsheet when trying to learn a new orgo concept. Get the basics down first, then …
  2. Figure out the “why” behind more complex concepts. You already have the basics down, so now it’s time to use them and apply them to figure out and “reverse engineer” the more complex problems that build upon your memorized basics. Try and solve for yourself what makes these things tick. Why does the example use this set of reagents in this situation? Another set of reagents would get you to the same end point — would you be better or worse off if you used the alternate set?
  3. Remember what you shouldn’t memorize! The oxymoron here is the trick to learning efficiently and effectively, especially in orgo. If you can get your bearings as far as what you should and shouldn’t spend your time memorizing, then that’s more time that you can devote to understanding the “why” behind orgo and not just the “what.”

Miko