Organic Chemistry, Nanny McPhee and Stockholm Syndrome

Learning is a complicated business. Learning organic chemistry is particularly challenging, because not-only do you have a lot of facts (the outcome of reactions) to learn. You face the additional barrier of having to learn a new language, that of molecular structure. Add to that the simple fact that molecular structures are inherently three-dimensional, and that the shape of a molecule has a very significant impact on its properties, and you start to appreciate the scale of the challenge.

Nanny McPhee is a wonderful allegorical film, released in 2005 and starring Emma Thompson in the title role. Nanny McPhee enters the lives of seven unruly children, and gradually (and magically) sets about imposing boundaries and expectations on their behaviour, to the point that they actually want to change. In many respects, Stockholm Syndrome (whether it exists or not) is at the heart of this film – the children certainly form a bond, and they certainly do not want Nanny McPhee to leave at the end (spoilers!!). But the consequence is a change in attitude/behaviour. The important point is that the change is gradual, and each step is manageable.

So what does this have to do with studying organic chemistry? And are the challenges unique to organic chemistry? I am definitely taking liberties here, but I find that students in year 1 and year 2 find organic chemistry to be very hard to assimilate. They definitely feel trapped and overwhelmed by the apparent volume of information that they have to learn.

Conversely, students in year 3 are becoming confident applying organic chemistry principles to unseen problems. Again, my choice of wording is very deliberate. It would be easy (but superficial) to say that they are ‘getting good’ at organic chemistry, but we really need to define what ‘getting good’ looks like. And then we need to define the steps that are needed to become competent.

Competence in organic chemistry can be defined as the ability to look at a molecular structure and to see the shape and expected reactivity of the compound. To be able to look at a reaction and to map out the individual steps that make up the process. To look at a target molecule and to be able to see which reactions you might use to make this molecule.

Let’s focus on the last of these goals. There is a significant cognitive challenge here. By definition, the people who are teaching this subject/skill are those who have become competent already. They inevitably had a level of talent that predisposed them to developing this competence. In order to look at a molecule, and to ‘simply see’ the reactions that could be used to make it, you have to first of all know the reactions, and to know what they can be used to make. This is a pattern. Chances are, the molecule you are being asked to make is not exactly the product of the textbook version of the reaction – you need to apply a bit of lateral thinking to apply the reaction to produce the new and modified compound.

What does lateral thinking actually mean? How do you set out to do it? It means solving a problem by a creative and indirect method. How do you do it? Well, you just do. You ‘just see it’.

Chance favours the prepared mind. It’s a cliché, and they are cliches for a reason.

Let’s take a brief diversion into neuroscience. The brain is not static. While we have a fixed number of neurons (brain cells) in the brain, we constantly build new connections – synapses – between them. You read something. You didn’t understand it. You look at the same material in another book, and you still don’t understand it. You become frustrated by your inability to understand it – ooh, chemicals released in the brain! After repeating the task and feeling the pain, suddenly it all clicks. And now, it’s so obvious, why didn’t you understand it before? Well, chances are, that effort has led to the formation of new synapses that allow the processing in your brain to take place. You have unconsciously programmed your brain to become good at that task. As long as you keep reinforcing the skill with practice (I am deliberately avoiding the term ‘revise’) you will reach a point where the skill becomes entirely unconscious. It is part of your ‘procedural memory’. Don’t think of this as just being things you ‘do’, like walk, or drive a car. Or, more importantly, think of the academic subjects you study as ‘things you do’ rather than as things you learn.

The key point here is that anything, no matter how ‘academic’, no matter how hard, can become something that you ‘just do’ without any conscious effort.

So where does this leave you, as a student of organic chemistry? Well, when you get to the point that you can solve any (reasonable!) organic chemistry problem with very little effort, there is no doubt that you will start to like it (Stockholm Syndrome!), and you won’t need someone like me looking over your shoulder and providing guidance (Nanny McPhee!).

The problem is, you don’t believe this will ever happen. That’s the bit I don’t really have an answer for! I wish I did! You’re just going to have to trust me. The most important thing is to keep ‘doing’ stuff. Draw structures. Draw curly arrows. Check your work against reliable sources. And the rest will (slowly) take care of itself.

Mark Elliott, written around 2022.

* There is some controversy about whether Stockholm Syndrome exists. I may be taking a little poetic licence.