Where Memorization Helps in O-Chem

by James

in Functional Groups, Organic Chem Study Tips

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. Here’s a quiz to get you started.

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. Using my textbook, I made these 5 quizzes in about half an hour.

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. Here’s a list for alkane and alkene nomenclature.

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.

Here’s a handy list of reagents.

 

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.

 

 

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{ 6 comments… read them below or add one }

Dave Blackburn

Memorize the vocabulary, not the reactions & relationships!
I tell my students that they have the choice of learning the positions of every leaf on a tree, or understanding the concept of roots, trunk, limbs, and twigs. If they get the concepts, the position of the leaves takes care of itself.
Nevertheless, the basic vocabulary as you list above is crucial!

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James

The tree is a great analogy, I’ll have to steal that! :-)

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Brett Reynolds

Hi, James! My brother, Michael, pointed me to your site. When you’re looking at vocabulary memorization (“paired associate learning”), there’s a good deal research into how to do that well. A lot of it has been rolled into a free website called Anki http://ankisrs.net/ (no personal interest).

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james

Hey Brett! nice to hear from you. I downloaded Anki and have started to use it for language learning. I looked into organic chemistry and it has some sections on functional groups and other topics, for those interested.

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red dragon

This is great advice I’ve done most of what you have suggested. Except I am having a difficult time remembering what reagent is for what. Any advice.

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Katlego

I think that memorization matters very much, in addition to understanding concepts, depending on the way in which your organic chemistry is being evaluated. For instance, at my school nearly one third of the evaluation consists in filling in the blanks. Essentially you are given either a starting material and reagents then asked to predict the product or given a product and arrow then asked predict the starting material and reagents. Because each reaction is worth seven marks, grading is very specific: the solvent, reagent, in some cases temperature and other conditions must be correct/in accordance to what was presented in lecture or textbook. Likewise, marks can be deducted for not specifying if the reagents operate in the same step or not, and detailing conditions such as wether the reaction occurs in excess reagent or in reflux. Although it helps to understand the mechanisms, on these questions no amount of thinking will help you determine that reduction with DIBALH in acetone occurs at -78C and not -88C or -68C. Nonetheless there are more interesting questions such as drawing mechanisms and predicting relative stability – but they only constitute two thirds of our evaluations. Likewise synthesis requires both knowledge of the reactions (none of which are provided) and understanding of their uses and limitations.

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