Regardless of where Organic Chemistry is taught, regardless of the genius and/or talent of the professor, and regardless of any variable that can be conceived, there is a percentage of students who will fail Organic Chemistry. The average midterm grade in Organic Chemistry ranges between 25-50%, hovering around 38% for classes having professors who challenge their students. Typically the first midterm includes concepts of acid-base chemistry, pKa, valence bond theory, Lewis structures, resonance, hybridization, alkane nomenclature, Newman projections and radical chain reactions. As the material is introduced, students of Organic Chemistry study in a manner identical to that which sufficed them since high school. Some periodically review their notes, and convince themselves they know the material. It’s not until 4 days prior to the first midterm that they begin working the problems.
The Art of Retrosynthetic Analysis represents a very powerful tool in synthetic Organic Chemistry, one indispensible in the assembly of complex natural products such as Forskolin and Rhizoxin D (two of my PhD research projects), Taxol and Brevetoxin. Even if one were gifted with the combined brain power of Sir Isaac Newton, Albert Einstein and Stephen Hawking, I guarantee that no chemist would ever be able to synthesize complex natural products without the application of retrosynthetic analysis.
A student’s first exposure to solving “puzzles” in Organic Chemistry “flies under the radar screen” somewhere around week 7-8 when SN1, SN2, E1 and E2 reactions are introduced. Albeit not apparent at the time, these puzzles are rather simple, and have to do with compounds containing 2° leaving groups, i.e. the ones that can go “either way.” Superior nucleophiles in dipiolar aprotic solvents react via SN2; strong bases in any solvent react via E2 (depending upon which book you read). Superior nucleophiles in polar protic solvents react via SN1 competing with E1. Solving the puzzle of the thing that goes “either way” involves knowing where the other factors in the “stew” push the outcome of the reaction.
Most points on Organic Chemistry exams are lost in weak areas that are highly preventable, i.e. areas requiring a constant “workout.” I’ve been keeping a mental tally for over ten years on where errors are routinely manifest, how they’re made, and how such errors can be avoided. You can read this article in less than five minutes, apply what is discussed, and increase the score on your next exam by a percentage directly proportional to the amount of energy you invest in strengthening certain areas.