Here we go again. It's the beginning of my undergraduate o-chem series. It's going to be a year of prose like this:

Recall the electron configuration of carbon (Figure 1.18). This electron configuration cannot satisfactorily describe the bonding structure of methane (CH4), in which the carbon atom has four separate C─H bonds, because the electron configuration shows only two atomic orbitals capable of forming bonds (each of these orbitals has one unpaired electron). This would imply that the carbon atom will form only two bonds, but we know that it forms four bonds. We can solve this problem by imagining an excited state of carbon (Figure 1.19): a state in which a 2s electron has been promoted to a higher energy 2p orbital.

Scintillating. I genuinely enjoy my subjects, but let's be honest. Right in the moment, there are many other things I would rather be doing than reading my chemistry textbook.

Recently, I explored whether it's possible to feel a sense of playfulness while you're alone. I found that it was. It it possible to feel playfulness while reading a chemistry textbook? Or is it better to optimize for an efficient, if dry, learning experience, and find ways to reward yourself afterward? If it is possible to feel playfulness while reading an o-chem textbook, it would be worth trading off at least some efficiency in favor of positive feeling. The question is how much. Of course, the best case scenario is where it's both possible to feel playfulness while reading, and it makes you learn more efficiently.

In my experiments of feeling playful while alone, I took away a few key insights.

  • Starting with an open, unfocused, non goal-oriented mindset was crucial.
  • The feeling of playfulness was based on connecting physical objects with memories, a sense of profound personal meaning, and possibility. There was a poetic, metaphorical, associative quality to the experience. These associations were neither purely spontaneous and involuntary, nor deliberately constructed. It was more a sense of resting my attention and gaze on an object, and then gently asking my mind to remember or imagine a psychological association.
  • I remembered the act of remembering afterward, and it made those memories more available to me in the future.

Playfulness while reading a chemistry textbook might take a similar form, something quite different, or simply be unavailable.

A particular difference is that my playfulness-around-the-house experiment was entirely visual. This will be, if anything, textual first and visual only secondarily.

Experiment 1

I read a couple review paragraphs about hybridized orbitals. I try to get out of the mindset of reading the text, and instead try to visualize it. My visual imagination is fairly poor, so mostly that entails looking at the diagrams and trying to "echo" them in my visual imagination. By practicing this a bit, I can see them in my mind's eye, and compare them with each other. I can directly see the point my textbook is making in words, but directly represented.

It's like the difference between having somebody explain different cuts in a diamond, or styles of brushwork in a gallery of paintings, and being able to directly perceive them yourself.

This doesn't feel "playful," but seems to be a step in the right direction.

Experiment 2

As I read another couple paragraphs, I notice that some sentences add something new to the visual. Others call attention to some feature that I'd ignored. Others don't affect the visual at all. By focusing my attention on the visual I've been generating and developing, rather than on the verbiage, my experience of reading this textbook feels different than it did before - more relaxed, more meditative. I'm having an interesting experience of what my visual imagination is capable of, rather than doing the labor of reading a certain number of paragraphs.

Certain words seem to suggest a visual representation, even though I'm not confident that it accurately depicts them. For example, the textbook says:

The larger front lobe enables hybridized atomic orbitals to be more efficient than p orbitals in their ability to form bonds.

What does that word "efficient" mean in a visual sense? Hybridized orbitals aren't a real physical process, just a mathematical description that more accurately predicts empirical data. I try representing this fact by imagining two hybridized methane molecules. One has shorter symmetrical orbitals. The other reaches out one end of its orbitals toward the surrounding hydrogen atoms, like an octopus extending four tentacles to grab on to some clams.

... Well, that's a fun image. Maybe I'll try to imagine bonds as octopuses and clams this year! And here's a little bit of genuine playfulness entering the picture.

This is all starting to remind me of my experiment with using a memory palace to try to memorize my general chemistry textbook.

Experiment 3

The shapes of small molecules can often be predicted if we presume that all electron pairs (whether bonding or nonbonding) repel each other, and as such, they arrange themselves in three-dimensional space so as to achieve maximal distance from each other.

I try to imagine this. At first, I get a picture that simply represents "small molecules," like a dot in my mind. Then my mind thinks of how squirrels will run around a tree, trying to stay on the opposite side of the trunk from you. Then it spits up a representation of yellow dots chasing each other around a spherical nucleus, in a similar style to the chemistry textbook. These imagines come up rapidly.

I'm starting to get out of the mindset of scrutinizing the words of these paragraphs, as if the language itself held the key to understanding. Instead, I rapidly "upload" the text into a visual image. This takes far less time. It's an attitude shift. Reading isn't about diligently shoving an imaginative aural simulation of the words themselves through your brain, or dragging your eyeballs across every line of text on the page. It's about activating your visual imagination and allowing the text to help you manipulate and notice features of those images. Sometimes that results in playful visuals, other times in geometrical reductions.

This is part of Valence Shell Electron Pair Repulsion theory. Last year, I'd have tried to remember this phrase by stringing together the sounds in my mind, like a jingle. Now, I just picture an atom, see the electrons in the valence shell, see them repelling each other, and the name just feels natural. It's the equivalent of naming a dock the "Place Where Cargo is Unloaded From Ships." The name isn't mysterious or hard to remember at all once you've visited, created a visual memory, and understood what's going on there.

Experiment 4

My imagination is starting to incorporate sound effects. I'm able to create transitions between simulated molecular shapes that feel sophisticated, sort of like a video game. There's a sense of being able to "click" a certain orbital to transition it back and forth between a bond with hydrogen and a lone pair of electrons. The sound effect and expansion as the bond with hydrogen turns into a lone pair, pushing the other bonds with hydrogen closer together, makes the significance of the different geometries more clear.

There's a physical satisfaction in being able to hold and expand on these images. It's a bit like the feeling of strength that comes after you've gotten into a long run and are no longer resisting the exercise, but instead enjoying the feeling of power residing in your body.

These visuals dramatically improve my ability to remember. The difference between an sp3 and sp2 hybridization looks insignificant when it's just these abstract abbreviations on paper.  But these two types of geometries look very different in their diagrams, and being able to quickly "flip" back and forth between imagining one and then the other is helpful.

The visual image contains all the information from the preceding paragraph. Thus, I no longer feel the anxiety I typically do about having forgotten the words in the first sentence by the time I get to the last sentence. It's all contained within the increasingly elaborate visual image I've been developing as I go along. A picture is worth a thousand words.

I'm not sure if this is taking longer than it would to just read the text. I suspect so. I'm also not sure if I'll retain the information better than by merely reading the text. I do feel as if I'm understanding it on an intuitive level much better, and to me, that's worth it. This is all review material, and I'm very curious to know whether this visualization practice will be a useful compliment, or even a replacement, for spaced repetition with flashcards.

Experiment 5

Why is fluorine the most electronegative element on the periodic table? The answer is that it has the greatest ratio of positive charge from the protons in its nucleus to the amount of shielding it gets from the electrons in its orbit. Picture those protons as black holes in the center of the atom, sucking in any electrons nearby. In a big fat molecule like iodine, there's a big huge cluster of protons in the center, but there are just as many electrons surrounding it "absorbing" that "suction," and what's more, they surround it in layer after layer, protecting electrons in nearby molecules from the force. In fluorine, there's not as many protons, but they have far fewer layers of electron "fat" around their core, so nearby electrons are much more exposed to their "suction."

Picture iodine as a big, content Roman patrician after devouring a feast. Fluorine is a skeletal, starving Windigo, ravenous and ready to devour the electrons of any atoms it can get its hands on.


Occasionally, the effort I put into visualizing the text produced funny or striking images, and felt like a form of poetic, imaginative mental play. Most of the time, it was a more calm and focused experience. Overall, though, making an effort to visualize makes the experience of reading a textbook much more satisfying. Now that I'm doing it, it's almost inconceivable that I would go back to doing things the old way - reading paragraphs and hoping that the verbiage somehow sticks.

Does this connect with playfulness, somehow?

When kids are playing, they're transforming the world with their visual imagination. A stick becomes a sword or a laser gun. Putting your arm up overhead like Superman and running around the room becomes flying. Telling a story creates a world in your mind.

Kids hurt themselves and fail in their efforts all the time partly because their imaginative world is more real to them than physical reality. When we decide we want to master physical reality, we start to focus on the world of our senses at the expensive of our imagination. This isn't bad, but the visual imagination appears to me to become incredibly important once again when we circle back around and want to explore the world in the greatest possible detail through science and mathematics.

My long-term perception of myself has been that I lack almost entirely the ability to visualize. Reading novels has tended to be an auditory and intellectual experience. This experience and others that I've written about over the last few months have convinced me that my visual imagination can be trained, and that this training is the number one method I have available to improve my general intelligence.

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4 comments, sorted by Click to highlight new comments since: Today at 11:57 AM

I like these posts, because it is good to see the process of working through things in their territorial glory rather than being provided a pre-polished map.

I am ~80% confident that if you could achieve the playfulness objective your mastery would be deeper than through the efficient method. I further claim that the dominant factor is not because it is less painful to spend the necessary hours studying. Two factors are higher than wrench-time based on my experience: one is that playfulness yields broad exploration; two is that play helps with durable memory formation.

This is driven by my experience with an electromagnetism theory course, where the play method brought me to a very high percentage score where I had barely passed the previous level of course using the efficient method customary to engineering school. A few key differences worth mentioning:

  • The efficient method in engineering school is essentially a procedure where you identify what information you can ignore, and then build time-efficient algorithms for each kind of problem you normally encounter. This is useful for churning through very high workloads, but fails badly whenever you encounter novel problems or problems with a gotcha in them.
  • I set the level of playfulness above the textbook, at the subject level; I never focused specifically on the reading of the textbook as the objective.

The subject is notoriously difficult, and the course in particular had a grim reputation because it was much more mathematical that the others in the curriculum. My early experiences with problems of that type consisted mostly of bashing my face against them until they gave, which took many hours. By the middle of this course, I had achieved comfort with the following procedure:

  1. Identify the topic, review the notes, engage in visualization of the topic (play).
  2. Attempt the problems.
  3. If stuck, withdraw from the problem and engage in play with the problem subject.
  4. Reattempt the problems.

This allowed me to routinely complete whole homework assignments in an hour or so, which was awesome. I was also able to successfully reconstruct derivations based on the intuitions I had developed through play and review.

Frustratingly I found it was necessary to develop this more or less independently for each course; I simultaneously crashed and burned on other courses because I couldn't get it to work. Damn you, microelectronics!

I'm very glad to see that you're learning organic chemistry!  It's a great subject for the type of exercise you've described, as it's a very visual field of study.  As you mention that visualization is a skill you're working on developing in parallel with your organic chemistry studies, I'd recommend that you get ahold of a molecular model kit.  It may sound silly, but having a physical model of a molecule in front of you can make a big difference in how long it takes to grasp why, for example, SN2 and SN1 reactions give different stereochemical outcomes.  

Organic chemistry can be a playful subject if you approach it with the right mentality (don't believe what the pre-meds tell you, and don't try to memorize your way through the first semester!).  If you're looking for ways to see how it impacts your life, try looking up the chemical structures of over-the-counter medications like aspirin, dietary supplements like vitamin B12 or taurine, or polymers like polyethylene terephthalate.  Relating a structure to basic sensory data (the feel of a plastic bottle in your hand, the aftertaste of aspirin) can help the subject matter feel more relevant.

Please feel free to reach out to me if you have questions about learning organic chemistry!  It's good to see someone posting on LW about a subject I feel qualified to comment on, for once!

Haha I may take you up on that! Thank you for volunteering :D These visualization techniques are also helping with my molecular biology class. Very general purpose.

This thing is even more fun when you have a "chemical machine" to make sense of :)

Once upon a time, when we were cramming for a plant physiology test, we looked at The Photosynthesis in all its monstrous glory, and it looked back at us.

And while the cycle of reactions which gainfully employ the carbons is relatively simple - more of knowing where you start and which atoms can be lawfully screwed off the molecules - the Dark Side proved to be more elusive. Had to imagine a system of catapults throwing The Electrons across a desert, operated by jinns fed by snacks falling from the sky (the snacks were signed in code, and the deceptively bigger numbers meant lesser energies)... Our teacher couldn't understand why we were grinning so hard at the questions...