Take “Don’t Memorize!” with a grain of salt

Loyal reader Sandy writes in with a comment about memorization:

I wish I had understood much earlier that there is a place for memorization in Orgo – like the reagents and what they contribute to a relationship, what reactions they are used with, etc. We were heavily discouraged not to memorize for the class – and I think it hurt my study plan. What we should have been told is “understand the mechanism – movement of electrons”, but you must memorize reagents, format of reactions, etc. I know he had good intentions, but he was not clear. It was at this point that I began to struggle. I did make an A, but spent the entire time between Orgo 1 and Orgo II reviewing and making sure I got the information I needed in my head.  This was the single most difficult issue I faced – trying not to memorize.

Great point.

No matter what anyone says, here’s where memorization helps: learning vocabulary, names of reactions/reagents/solvents, abbreviations, nomenclature, functional groups, and the bond-forming/bond breaking pattern of each class of reaction.

In short: vocabulary, conventions, and results obtained by experiment. Anything that answers the question “what?”is something that can be memorized. 

Where memorization doesn’t help as much is in answering the question “how?”

• how would you use [this data] to determine [this property of a molecule] ?
• how do you synthesize [this molecule] from [these molecules]?
• how will changing [this property of a molecule] change the [property of this reaction]?
• how will [this molecule] react under [these conditions] compared to [these conditions]?

See what’s going on here? We’re changing two variables at once, and the number of  possibilities (and things to memorize) increases exponentially. This is where applying concepts just becomes more efficient than memorization. I think this is what’s behind instructors’ advice to “not memorize”: it’s sound counsel.

In the best organic chemistry courses, you’re taught to apply the concepts you’ve learned to solve problems. So one piece of advice for students : ask the “how” questions a lot.* (“How does this reaction occur” is a subtly different question than “what’s the mechanism of this reaction”!).

* “Why?” is also a good question to ask, although the answer can sometimes be unsatisfying. (example “Why do we use [this reagent] for this reaction?” “Because it’s convenient, reliable, and cheap”!]