How to study organic chemistry 2

Sort reactions by reagent and mechanism

Memorising every reaction on its own fails as soon as the exam asks for a route from A to B. Group reactions by reagent (what does LDA, NaBH₄, mCPBA do?), by mechanism (aldol, Claisen, Michael and Robinson are all enolate chemistry) and by the classic pairs of mistakes (Markovnikov vs anti-Markovnikov, kinetic vs thermodynamic enolate).

Retrieve, mix, space

Testing yourself and spacing practice over days are among the most effective techniques, rereading and highlighting among the weakest (Dunlosky et al., 2013). Mix reaction types when practising; mixed practice is harder but leads to better results (Rohrer & Taylor, 2007).

Practise syntheses

1. 1

   Work backwards from the target

   Which bond is new, and which reaction forms it? That is the last step.

2. 2

   Draw the intermediate

   Draw it first, then pick the reagent.

3. 3

   Check every step

   Does the reagent react elsewhere in the molecule? Then you need a protecting group or another order.

Sources

• Dunlosky, J., Rawson, K. A., Marsh, E. J., Nathan, M. J., & Willingham, D. T. (2013). Improving students’ learning with effective learning techniques. Psychological Science in the Public Interest, 14(1), 4–58. doi:10.1177/1529100612453266
• Rohrer, D., & Taylor, K. (2007). The shuffling of mathematics problems improves learning. Instructional Science, 35(6), 481–498. doi:10.1007/s11251-007-9015-8
• Cepeda, N. J., Pashler, H., Vul, E., Wixted, J. T., & Rohrer, D. (2006). Distributed practice in verbal recall tasks: A review and quantitative synthesis. Psychological Bulletin, 132(3), 354–380. doi:10.1037/0033-2909.132.3.354