The Philosophy of Organic Chemistry

What Constitutes this Philosophy?

What is the philosophy of organic chemistry? Consider this. No one ever sat down and arrived at knowledge of organic chemistry a priori (by thought alone) and no one ever will. In contrast, one can just sit under a tree or in a hammock and with a little focus, reach geometric truths by thought alone—the sum of the angles in a triangle must add up to 180^o and the degrees in a circle, 360^o—no observation or experience is required. This is despite the fact that you have never and will never experience an actual triangle or circle. While some objects and representations remind us of these things,  a circle or triangle cannot be experienced. Most things in geometry can be imagined but don't exist.

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ammonium isocyanate[/caption]

In contrast, chemistry and particularly organic chemistry is pure empiricism requiring observation and experiment as even common experience tells us almost nothing about what it is. Molecules can be detected with the senses but even the question of what organic chemicals are or are not was mired in a prevailing belief that living things in some vital way are metaphysically distinct from non-living things. This was hotly debated until 1828 when urea, a biological compound was synthesized in the lab from an inorganic salt (click image to view).¹

Even well into the early 20th century, all of our knowledge of matter and the true nature of atoms triggered heated battles between schools of thought about the dual nature or dichotomy, to be more precise, of behavior at the atomic level as particle-like versus wave-like.

Organic chemistry, all of it, must become known either by observation with the senses; or by other aspects of the subject that are simply governed by agreed upon human conventions that are statements of convenience not matters of fact as many indoctrinate themselves to think and want to believe.

In order to learn Organic Chemistry, skill-building attains through sustained practice often before it is understood. Thus, learning organic chemistry can be a paradox. This is the reason so many beginners talk about how difficult the subject is—yet the same people can hardly pinpoint why. It's assumed that it's because "there's too much to memorize" or they have "problems with three-dimensional things". Those sound like reasons but obviously, it's not that simple. That is an illusion and the main reason many don't or never "get" it.

The mental skills are gradually acquired through the traditional hit-or-miss approach and mostly trial and error by working problems (having a good instructor doesn't hurt either).  Each place where you get stuck truly feels like a dead-end with nowhere to turn. There's an even simpler reason for this. You can't learn it unless you practice—however to practice you have to learn it. Often it is almost whimsically or covered in no logical order making the undertaking to learn it seem like a vicious circle. So most people only attempt half of the circle.

How does one practice a discipline one doesn't know in order to learn it? The practical answer is: as quickly as you can.

The disparities between the topics in organic are numerous and wide-ranging; shifting gears constantly from week to week or even day to day. From chemistry essentials, to nomenclature, to acidity (which is never given the treatment it deserves), to spectroscopy, to isomerism, and more—students each have their own idiosyncratic preferences and aversions to each of these "gears".

Some tend to be better at nomenclature, others abhor it; some enjoy spectroscopy, and others can not stand it. This back-and-forth can and does cloud the actual point. The bigger point which has nothing to do with memorizing alphabet soup.

All of these free-floating pieces of information lack coherence to the learner. Your goal, which sadly not everyone reaches, isn't just a good grade but the unification of all those pieces.

Yes, yes, I know. You're thinking that's true of every subject. Make no mistake about it: nowhere is this absence of unity more pronounced and confounding as in the subject of organic chemistry.

...Learn Philosophy on Top of Organic Chemistry?

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...philosophy? what?[/caption]

No, not quite. It's not the way it sounds. Philosophy may evoke imagery of the really involved and deep questions about, well, everything there is. But you and I already know and use philosophy daily. We have to.

Philosophy is the only college discipline you must do whether you study it or not—though it was, at one point, this is not a biased statement (it was a major of mine). You don't have to study chemistry, biology, or business.

You can study whatever field you wish to enter. But you must make critical decisions and you must think logically to survive. You must decide between morally responsible and questionable choices in the hope of understanding how to live a good and examined life. If you don't care about those things, why bother with college and loans and challenging yourself?

Whether we choose to be or not, we are all philosophers. The branch of philosophy that deals with the nature of knowledge and all related things is called Epistemology.

Science itself was known for centuries as natural philosophy. Some claim that philosophy is a subsection of science and that assertion is backward. Really, natural philosophy is still what science is. The scientific method and science itself is a tiny and very important facet of a much broader field of philosophical inquiry about what it is that constitutes the reality around us.

The philosophy of chemistry is even more finely divided as I've personally learned and taught it and organic chemistry is even more fine.

There are several components about what we can and cannot know or learn, most of which no one considers. The gist of the philosophy though can be explained in about a week. Whether it sinks in with any depth in that brief time is personal. Through a variety of media and tools our hope is to bring that to light; and not in the traditional way that a textbook or series of class lectures has proven since the 1950's to be a failure, (45-60% failure rate). We are here to elaborate on this philosophy as much as possible and in the most direct way to render it into a method in the tradition of Descartes.

Why A Philosophy of Organic Chemistry is Needed

Almost no one presents a unified philosophy behind the very important aspects of organic chemistry. I am talking about the core of the subject (and of your grade). That is, predicting products, rationalizing mechanism and chemical change, exploiting trends to the fullest, visualizing and drawing it with clarity, and having the confidence to just sit down and, well, to crush any problem in your path.

The facts and details are in every edition of textbook. Summaries are everywhere and almost nothing new exists—not at this level. Lists and summaries of reactions...you have them already; they conclude every chapter. Many people still believe that knowledge is gained by memorization of alphabet soup. No such jumble of facts is a method. I personally was expected to learn it from the worst, tangled-mess-nightmare-excuse-for-a-textbook ever written (out-of-print, thankfully). It still makes me cringe to think about it. The chapter on hybridization started with a question about norbornene. Ridiculous!

You Must Rely on You

Invariably, textbooks present in such a way that doesn't make sense to a critical thinker and certainly not to a casual reader who is accustomed to linearity, trains of thought, and the elaboration of ideas, not a series of factoids. The problem I learned early on in graduate school while supervising and instructing undergraduates wasn't what the book contained but what it didn't contain and never contains...like most books published today.

As I said before, I hated my organic chemistry textbook. I was absolutely frustrated by its presentation and that engendered a deep hopelessness I'd hadn't experienced before academically. I felt doomed to failure. Even worse, the professor was, in the truest sense, a sadist who cared nothing about teaching and only doing research. He soon left with full tenure to a different university in Baltimore by virtue of his research accomplishments. Good for him but he could not teach his way out of a paper bag nor did he want to. He loved to hear himself talk however. I didn't even realize until I was in graduate school he was teaching graduate level material to us. He couldn't relate to anyone who didn't think like him. I knew he was a jerk, but to step it up several notches, for whatever reason, was like being a punching bag for someone's ego.

It was just happenstance how I recovered in the class. I mainly didn't absorb the subject from the textbook and certainly not at all from the professor. I learned it mostly by talking with other students trying to explain it through late-night, sometimes all-night, sessions and working problems non-stop even though that book had no solutions manual.

Without question, the presentation of Organic Chemistry is scatterbrained (that's the nature of this broad subject) and the reading itself, every hard-fought sentence of it, takes time to trudge around or though, which makes piecing it together seem like an endless and sick joke particularly when it gets really abstract. If this sounds like hyperbole, when you come to the revelation of how simple it actually is, how much is unnecessary, which will be demonstrated, you will understand just how heuristic, how cautious, I am here in trying to understate the glaring problems the average student faces. It simply doesn't have to be this way.

What We Do

The good news is that the philosophical part I'm talking about is not difficult to learn. There are guidelines and a method that aren't complicated. It works and is certainly better than the alternative: attempting organic chemistry with no real basis of thought, no concern for unification, just repeated, sad, time-consuming attempts to absorb dumbed-down, error-prone videos (rambling snippets), re-hashed summaries, awfully written analogies to some kind of alien language when it is just chemistry. These seem to be everywhere. All of that information is in every chapter, of every book already. The goal (your goal) is to use your book as a reference by focusing on straightforward, reliable methods and allow the procedure to materialize with practice.

The other, painful kind of approach which people have endured for decades is the reason many pass the course and later swear up and down that they learned nothing but jargon or how to pronounce terms like Grignard. People are relieved to be done though they certainly don't continue on in the subject. Those who do it using a rational foundation however, love it. Mine is such a story. I didn't start college as a chemistry major. Far from it! And I certainly never planned to become an authority in organic chemistry. I didn't do well on the first exam and slightly worse on the next. I had a sadistic professor, yet that just ignited a fire within me that turned my world upside-down (in hindsight, for the better). And I can show you how I did it.

Take comfort in the fact that understanding these fundamentals which aren't taught is what makes organic chemistry difficult but with a strategic mindset, this philosophy makes for a rewarding and I dare to say, enjoyable experience. I've witnessed it personally hundreds, even thousands of times. Nothing gives an educator quite as much satisfaction. To do it and make it accessible is what we do.

The other biggest obstacle, by the way, is unlearning the things you thought you knew about chemistry. This may come as a shock to you but you have no real idea, possibly just a faint notion about important concepts, definitions, of even simple things like acidity. In this course you will apply all that in numerous forms. I'm paraphrasing a famous speaker with the following: "It isn't what you don't know that hurts you most. It's what you are certain is so, that simply isn't." Even more of an obstacle is what most people I see struggling do: trying to learn organic chemistry at the pace with which they are accustomed to learning other subjects. Bad idea. They try to be fast, learning one thing then the next, doing problems in a similar way (racing to the answer) and end up one to two steps ahead of themselves which eventually gets them nowhere at all.

These problems and their remediation are incorporated into a method that took years to synthesize. If you use it, it will help you overcome the hurdles in your journey through the wondrous subject of organic chemistry.

The Big Picture

Only in hindsight when you've reached the level of philosophical inquiry will this become clear—not every detail however...as that's not ever typical in the first go-around. Even long-time professors, luminaries in the field, like my PhD adviser who was a walking, talking database. However, even he, indeed, no scientist knows it all. What matters though is what I refer to herein as the big picture. When I happened upon it, I was not reading or studying but just walking across the sun-strewn grass of the quad to eat lunch, when it all just "clicked" together.

It was the most intellectually satisfying, the loudest clap of thunder, and that epiphany, having struggled so long with precious little progress, to this day, reverberates. Did I know it all? Of course not. But I got the point. All the organic chemistry knowledge I accumulated thereafter in graduate school and over years of teaching still don't compare to that moment which were refractory details in comparison.

The big picture can and should be attained in the first year and hopefully before the end of the first semester. That is what all learners should focus on. You do not want to enter Organic Chemistry 2 without the big picture or worse, face an entrance exam a year or two later without that foundation. By then, it's back to square one.

We forgot how difficult it was to learn to speak as toddler's. In hindsight, we look back and think it was effortless. Our parents, on the other hand, thought it was miraculous. We forget the hardship of learning to walk and that is was learned through hardship. It is not unlike learning Organic Chemistry. You will stumble here and there, you will feel unsteadiness and uncertainty—perhaps the entire time until you reach the big picture. Actively seek it out. When you reach that point where you can philosophize rather than parrot what you've heard or read, you will simply never get enough of it because the subject will be like the ones you're accustomed to but feels  all the more rewarding. The point of all this is to minimize the uncertainty because the big picture is there. It's waiting for you and is a remarkable thing once found.

[1] Graphic Credit: Wikiwand/Wikipedia (under Wohler, Friedrich)

Continued: The Philosophy of Organic Chemistry (Part II)