Where Memorization Helps in O-Chem

Although in my last post I basically poo-poohed memorization as a study strategy, I don’t mean to imply that it does not have its place. Although those of us for whom organic chemistry is a full time pursuit would like to imagine otherwise, students are often in a position where they are juggling a great number of other commitments, including time-intensive courses, labs, and of course, midterms. I was amused to hear from one of my students last night that he spent the better part of the weekend in a comparative anatomy lab with a dead cat, shark, salamander and sea lamprey in an effort to cram almost 500+ different pieces of information into his skull for an exam this week. And he also just took a new job in a research lab.

With such hectic schedules, it is not surprising that courses like o-chem can get pushed aside until the last minute. And when that last minute arrives, it is often spent in a flurry of memorization – of reagents, nomenclature, trends, and vocabulary. Too many students, however, spend time memorizing specific reactions – like the reaction of, say, cyclohexene with Br2 – and get thrown for a loop when a slightly different starting material is used.

My advice to those who memorize: if you’re going to do it, at least do it right. Focus on things that are relatively non-conceptual, like these four topics. Then use the remaining time to learn the concepts, and finally work on problems to solidify them.

1) Functional groups

Getting their names and structures straight might initially seem as difficult as keeping track of all the characters in a long Russian novel, but it’s a must for doing well in organic chemistry: nearly all the reactions you learn will involve some kind of interconversion of functional groups.

2) The Lingo

Diastereomers. Olefins. Tautomers. Gem-diols. Listening in on a conversation between organic chemists can sometimes make you feel like you’ve somehow landed in another country.  If you’re finding yourself having a hard time picking up the language, it might be worthwhile to make a list of vocabulary terms from the textbook and start going through it. With all the online tools available, it’s a snap to make something like this for yourself. 3) Certain aspects of nomenclature.

L-proline. (+)-tartaric acid. (R)-2-butanol. There are lots of new nomenclature conventions to learn, and you’re going to be expected to understand what they mean. Here’s a collection of some of the oddities.

4) Getting acronyms and abbreviations straight

Before you can understand how something works,  you have to be able to at least identify it. If you’re completely at a loss as to what DIBAL, THF, and PCC stand for, or what OsO4, mCPBA, and NBS do, it’s good to have a list of common abbreviations (along with functions) ready just in case you forget.  With that basis, you can go spend more time on actually understanding the reactions themselves.

For students in a hurry, using memorization techniques can be a quick way to lay down a foundation of vocabulary and structural knowledge, setting the stage for focused attention on learning and applying concepts.

It should be noted that in order to really harness your memory, it will help to engage as many parts of yourself as you can – speaking out loud and writing will give you much better results than quietly reading to yourself.