Ace Your Next Organic Chemistry

With these Downloadable PDF Study Guides

Our Study Guides

Organic Chemistry Study Tips

By James Ashenhurst

Learning vs. Memorization In Organic Chemistry

Last updated: April 15th, 2019 |

“Learn the concepts! Don’t memorize!”.

It’s one of the most common sentences found in the many examples of instructors’ essays on “How to Succeed in Organic Chemistry”.

But what does it really mean? It took me a long time to figure that out. But I’m going to try to explain it with an example.

Let’s take two students with different study strategies.

One of them focuses on memorizing facts, reactions, and numbers.

The other one focuses on understanding the trends that lie behind those facts, reactions, and numbers.

They’re given a test with a question like this one:


Which strategy will do better?  The student who focused on memorization would have known from a pKa table that alkynes are more acidic than alkenes, which are more acidic than alkanes. The second student, knowing acidity trends,  would be able to recognize the fact that the hybridization of the carbons in the alkyne, alkene, and alkane are sp, sp2, and sp3 respectively, and would know that acidity increases as you increase the amount of s-character in a bond since the electrons are stabilized by being closer to the nucleus.

Both memorization and a concept-based approach would work for answering this question. The difference is time: It takes longer to gain an understanding of what is going on rather than just memorizing a group of numbers. Last-minute crammers, understandably, go for the memorization approach.

Now change the question to either one of these two:


Who will do better now? This type of question will destroy the memorizer, because you won’t find values for these acidities in textbooks. It’s just too obscure. However, the student who focused on learning the concepts could answer this question without having put in additional time to study – because it involves applying the same concept that was applied in the first question. **(note at bottom)

There are definitely organic chemistry courses where the instructor favors a pure regurgitation based exam style. If you’re taking a combined one-semester course in organic chemistry with little to no focus on mechanism, a pure memorization approach might actually work.

However, at a more advanced college level, instructors will have higher expectations and have developed testing strategies designed to thwart memorizers.

In short, while memorization might be effective for you if time is short, it is a fragile strategy that can easily be beaten by a professor who is intent on testing concepts.

** note on these questions: since acidity increases as you go from sp3 to sp2 to sp, basicity will *decrease* as well.  So sp-hybridized oxygen is less basic than sp2 hybridized oxygen which is less basic than sp3 hybridized oxygen.

Related Posts:


Comment section

6 thoughts on “Learning vs. Memorization In Organic Chemistry

  1. Nice post. I still think that memorization definitely helps more than we sometimes give it credit for, especially in fields like chemistry and biology where there are a large number of empirical facts not derivable from first principles. Many of the leading chemists like Woodward, Pauling etc. were also known for the vast amount of literature they had memorized; these facts would serve as a reference point for thinking about other matters. So if you do have a good memory you should certainly put it to good use while remembering, as you said, that understanding should have a higher priority.

    1. You’re right, it is a really curious mixture of memorization and conceptual thinking. I’m going to write a future post about some of the ways in which memorization can really help.

  2. I don’t think we need to memorize like Pauling and Woodward, we have ipads now! but no technology can replace our understanding of concepts, because only then are we able to pose new questions.

  3. For question 2, with the nitrogens, isn’t it more complicated than just the orbitals? I get That the tertiary amine would be the least acidic. But when you compare the conjugate bases on the other two wouldn’t the resonance of the ring stabilize the c.base more than having the charge localized in one sp hybridized orbital?

    1. No, because in the example of the ring, the lone pair is not in the same plane as the pi-orbitals in the aromatic ring and is therefore not resonance stabilized. This is a classic trick question in the aromatic chapter. There is also no resonance stabilization in the nitrile case.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.