Why Take Organic Chemistry? Part 5

Educational Significance 

My colleague Peter Beak makes a valuable observation:

Too many students are unable to make the transition [from algorithmic to non-algorithmic approaches], and while not literally failing the course, miss the opportunity to develop an important professional and intellectual skill at this point. For those who are flexible and capable in problem solving, the course can be a turning point in intellectual development.

I am motivate to teach in a way that will help more of my students realize this turning point.

Why Take Organic Chemistry? Part 4

Risk, Failure and Uncertainty - An essay on the habits and attitudes beneficial to solving complex problems

On the Role of Memory - Practice and Repetition

Throughout high school and possibly even in their first year of college, rote learning served my students well. Their past success encourages them to stick with what worked. And so, it's not surprising that many will try to rely heavily on a memorization-only approach when they begin organic chemistry. But memory alone will not suffice! Complex problems are challenging, in part, because they are new to solver; the solver has never before charted a solution to the problem at hand. Since the problem is new, it follows that the solver’s memory provides no record of the complete solution. And while memory alone cannot possibly provide a complete solution to a complex problem, a strong and productive memory does help the solver by allowing him / her to quickly generate relevant options at each step of the iterative process. Here it may be helpful to distinguish memorization that is productive from rote learning.

Rote learning is the act of storing information without meaning. To realize fast recall and to make proper connections, it's essential not only to have a wealth of relevant facts in one’s mind, but also to have those facts organized in an orderly manner. Rote learning fails to achieve this. Structured information, on the other hand, provides insight and a deeper level of understanding.

So how does one acquire a rich memory that is organized for solving complex problems? The answer is practice and repetition. By practicing a variety of complex problems, students are exposed to a wide range of fact-filled experiences. With repetition, they'll learn to construct associations and recognize patterns. In other words, practice grows their information warehouse while repetition organizes it. Practice and repetition are thus effective means to a strong and productive memory. And unlike rote learning, this memorization technique does help solve complex problems.

The role of memory is easily seen by comparing students with strong memories to those whose memories are deficient. When students with poorly developed memories reach into the information warehouse to generate initial-step options, they cannot find what they need, either because it’s not there or because the facts are not well organized. These students tend to grab and use whatever they find. The result is a poor set of initial-step options and almost certain failure. These students are relying on intuition that's biased because their information warehouse is limited or in disarray. In contrast, students who perform best have practiced solving complex problems over-and-over again. Having an extensive collection of organized facts, these students are able to reach into their memories in the heat of the moment and quickly find what they need. You might say they are developing "accurate intuition".

In tomorrow's post I'll conclude with a brief remark about what I see as the long-term educational significance and how my thinking will influence the way I intend to approach this coming year.

Why Take Organic Chemistry? Part 3

Risk, Failure and Uncertainty - An essay on the habits and attitudes beneficial to solving complex problems

The Iterative Process of Solving Complex Problems 

Refer to the graphic from yesterday's post. The process begins by generating initial-step options symbolized by letters A through Z. The initial-step options are created by using various techniques, or possibly by repeated application of just one technique. Consciously or unconsciously, expert solvers do the same when they attack such problems. For the expert solver, however, just one initial-step option is usually all it takes, being created intuitively and accurately from years of experience and stored information. But even the expert must follow through the iterative process to validate his/her initial-step choice. For the novice solver (my students), several initial-step options probably need to be considered. If the novice uses his or her intuition, the initial-step options are almost certainly biased by a limited experience-base, although s/he still might intuitively produce an acceptable choice. Alternatively, the novice may draw upon a 'rule of thumb', a guideline s/he learned to associate with some special feature in the problem's starting point (e.g., "whenever you see this, do that"). If you think 'rule of thumb' sounds like an algorithm, you're correct. However, remember that the 'rule of thumb' only provides an initial-step option, rather than guaranteeing a pathway to a solution. Other techniques commonly used to generate initial-step options are reasoning-by-analogy whereby a complex problem is seen in relationship to another problem whose solution is known. If all else fails, a slow, detailed and deliberate analysis is pursued which, for organic chemistry, might involve a bonds-made, bonds-broken association chart. This list of techniques isn't exhaustive (e.g., try working backwards from the solution), but the list represents the common approaches to create initial-step options.

Next the solver must choose an option from those created. It is very possible that one of the initial-step options stands out as better than the others, but it is also possible that none of them appear more reasonable than the others. It is also possible that the solver has yet to consider the correct initial-step that leads to a solution; only time will tell. The solver must now take further action since inaction gets him/her no closer to a solution. So, a risk must be taken - a choice must be made - an option must be pursued. With the initial choice in hand, the solver performs further action on the initial choice to advance it toward a solution. This "something" might be to create another set of options - the secondary-step options - using the techniques outlined above, possibly with the aid of field-specific tools (e.g., organic chemists might use curved arrow notation). Once the secondary-step options are created, an evaluation is made by comparing the developing solution to the targeted solution, to see if there is an obvious pathway to completion. If no clear pathway to the targeted solution is yet in sight, the solver must contemplate defeat or face the uncertainty of continuing onward. If the developing solution shows obvious shortcomings, the solver may accept failure and return to the initial-step choices, beginning the entire process again, possibly by creating an even larger set of initial-step choices. Alternatively, the solver may decide to proceed onward through uncertainty by generating another round of next-step options and further evaluating the result. This iterative process continues until a solution is reached.

The challenges are obvious: successfully generating a sufficient number of options, overcoming narrowness that results from biases, continually making choices from a growing and tangled web of options, knowing when to cut one's losses, and knowing when to continue to plow through uncertainty are all very daunting, especially for the novice. So how does the novice become more like the expert? S/he acquires a set of experiences that produce accurate intuition. This takes concentration, persistence, adaptability and regular practice over an extended time. The gratification realized as the solver develops expert-like intuition is incredibly rewarding, but it comes slowly. Those novices who become successful solvers are probably comfortable delaying their gratification.

The tomorrow's post I'll present my views on the role of memory in solving complex problems.

Why Take Organic Chemistry? Part 2

Risk, Failure and Uncertainty - An essay on the habits and attitudes beneficial to solving complex problems 

A Framework for Solving Complex Problems 

The title change that I mentioned in yesterday's post is likely to significantly alter my approach to instruction. For example, I will be more deliberate about teaching a framework to help my students navigate their way through problem solving. The framework I have in mind is sketched at the right (click on the graphic to enlarge). For now, just appreciate that the graphic highlights the attitudes and habits that students must develop in order to meet the challenges associated with solving many kinds of complex problems, including the ones encountered in organic chemistry (e.g., in organic chemistry, these are multi-step synthesis or multi-step mechanism problems).

Most of my students entered college trained to attack problems by memorization and plug-and-chug, i.e., algorithmic approaches. A major goal of college teaching, in my opinion, should be to reprogram this mindset. It seems important to make students aware - from the very outset - that the problems they'll encounter in organic chemistry class are different than what they're used to. Organic chemistry problems require solutions that are multi-step, multi-faceted and non-algorithmic. Nobody solves these problems by memorization alone. Nor are solutions found by applying a simple formula. The pathway to a solution - the main point to take away from the graphic - involves risk, failure and uncertainty. Getting used to taking chances, overcoming setbacks, and developing confidence to move through doubt, are the most valuable experiences the students in my class will encounter. Becoming comfortable with these experiences will help them confront the kinds of problems that are sure to fill their future professional careers.

Study the graphic now, and in tomorrow's post I'll give a more detailed description of this problem-solving framework.

Why Take Organic Chemistry? Part 1

Risk, Failure and Uncertainty - An essay on the habits and attitudes beneficial to solving complex problems 

A Reevaluation of Instructional Objectives 

For the past 13 years I've taught a two-semester sequence of introductory organic chemistry to students at the University of Illinois, Urbana-Champaign. The majority of my students are pre-professionals and most are not chemistry majors. While the format and means by which I deliver these courses has continually evolved, I have - until very recently - held steadfast to the idea that the organic chemistry content is the most important objective of my teaching. I was fully aware that the problem solving skills which students acquire are important too, but problem solving, as an intentional part of my instruction, took a secondary role to rigor in the subject matter. For the reasons explained in the upcoming posts, I've flipped the importance of these two instructional objectives. In fact, if I were to re-title the course today, I might call it, The Skills of Complex Problem Solving Learned Through the Study of Organic Chemistry.

The new title suggests that problem solving should supersede course content as the primary instructional objective. In this light, organic chemistry content is the means to acquire better problem solving skills. A course which develops the habits and attitudes beneficial to solving difficult problems is likely to produce greater value for the majority of the students enrolled in my course. After all, learning to solve problems, particularly the kind of complex, open-ended problems encountered in organic chemistry, has relevance and meaning to every future professional.

In tomorrow's post I'll illustrate a framework for solving complex problems.