Organic chemistry

Organic chemistry: memorising reactions is why it feels impossible

Organic chemistry has a reputation as a memorisation nightmare, and for students who try to memorise it, that reputation is entirely earned: there are hundreds of reactions and you will not hold them. But the students who find it manageable are not memorising more. They are memorising far less, because they learned the mechanism instead of the outcomes.

6 min readSubjects

One idea, applied over and over

Electrons move from where they are abundant to where they are scarce. Nucleophile attacks electrophile. That is essentially the whole subject, and every reaction you are asked to learn is a specific instance of it wearing a different costume.

Memorise the outcome of a reaction and you can answer questions about that reaction. Understand *why the electrons went there* and you can answer questions about reactions you have never seen — which is what the exam will show you, because the examiner knows perfectly well who memorised.

Arrow pushing is the whole skill

  • Draw every mechanism by hand, with arrows, from memory. Not reading them. Drawing them. Arrow pushing is a motor skill and it is learned the way motor skills are learned.
  • Say what each arrow means out loud — this pair of electrons moves from here to here, because. An arrow you cannot justify is an arrow you copied.
  • Predict the product before you look. The generation effect is free and organic chemistry is the ideal place to use it.
  • Then do it backwards. Retrosynthesis is where understanding is really tested, because there is nothing to pattern-match against.

What actually needs memorising

A little: reagent names, a handful of specific conditions, some pKa values, the named reactions your course insists on. Card those on a spaced repetition schedule and stop trying to memorise the rest — it will not fit and it does not need to.

Common questions

How do I stop memorising organic chemistry reactions?

Learn the mechanism — nucleophile attacks electrophile, electrons move from rich to poor — and derive the reactions. Understanding lets you answer questions about reactions you've never seen, which is what the exam shows you.

Why is organic chemistry so hard?

Almost always because it's being studied as memorisation. Studied as one idea applied repeatedly, the volume collapses dramatically.

How do I get better at arrow pushing?

Draw mechanisms by hand from memory, and justify every arrow out loud. It's a motor skill plus a reasoning skill, and reading mechanisms trains neither.

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