Studying Organic Chemistry ---
Frequently Unasked Questions

I heard that this is a difficult course. Is that true?

Yes and no.

What do you mean?

The difficulty with the course is that you will have to master a very large volume of material to do well. In this regard, this course is difficult and may be unique to your experience so far. It is also true that the ability to visualize molecules in three dimensions is very helpful. If you do not have this ability, you will find some of the material more difficult. However, the use of appropriate aids, such as a molecular model kit, can at least partially compensate for lack of a stereo-imagination. Finally, at times you will be called upon to make use of several concepts and facts simultaneously to solve problems.

On the other hand, most of the concepts are pretty straightforward. So, if you work at understanding them, you very likely will. Edison's comment about genius being 2% inspiration and 98% perspiration is germane. You do not have to be an Einstein or a Pauling to be successful, but you do have to work hard. Furthermore, formal mathematics is used very little in this course. So, if you had difficulty in general chemistry in converting word problems into the appropriate mathematical expressions, you will not encounter much difficulty of that sort here.

How hard do I have to work?

This depends, of course, on your talent for learning the material. If you have a knack for it, you will learn it faster, and, if you do not, it will take longer. [I think it is one of the tragedies of life that those things we do well and enjoy are the very things we can do quickly, and conversely, those things we do not do well and do not enjoy take more of our time. In this regard, it should be quite helpful to you to get interested in the material; your attitude can definitely work for or against you.]

To give you a more concrete answer, I have in the past asked successful students how much time they spent studying for this course. The consensus seems to be about 14 hours a week, or two hours a day. This is in line with a common study-time recommendation that you spend two hours studying for each hour in class (3 hours of lecture plus 4 of lab = 14 hours of work outside of class). I would also suggest that you do this in two daily one-hour sessions, if possible. And, when studying, you should do just that and not divide your attention between studying and other activities.

OK, OK. I get the picture. I'll probably have to bust my ass for an A. But can you tell me the most effective ways to study?

I'll try. But remember, we're all somewhat different. So, if you find something that does not work, try something else. Don't keep repeating the same unsuccessful approach.

First read the material in the text with the idea that you will try to understand all of it. But do not try to memorize a lot of it at this time. The key on the first go-through is understanding, not mastery. But don't let things you don't understand slide, thinking they are unimportant. This first reading is best done before the material is covered in class, so you can ask questions about anything you don't understand.

Reread the text material. This time you want to remember anything that is important. How do you know whether you have remembered the equation for a reaction, a reaction mechanism, the structure of the sec-butyl group, or whatever? Close the book and write it on a sheet of paper. Open the book. If you wrote the same thing that is in the book, you know it (at least for now). If they are different, you don't know it --- PERIOD. [An aside: It is very easy to be taken in by passive recognition. An example of this would be if someone started to say, "Four-score and seven years ago ...," you would immediately recognize (passive recognition) this as Lincoln's Gettysberg Address. But you don't KNOW the Gettysberg Address; you couldn't write it down. Passive recognition and knowing something are quite different. Knowing organic chemistry will pay off on the exams. Passive recognition will not be worth much.]

When you think you have mastered the material --- you understand it and think you remember the important items, do the problems and check your answers (there are probably a few errors in the answer book, so if you think you're right and the book is wrong, check with me). If you solve a problem correctly, you have probably mastered the material that relates to that problem. By the same token, if you have not solved a problem correctly, you have not mastered the material that relates to that problem. Don't let it slide; reread the material in your text and class notes that relates to the problem and rework the problem. If you cannot get it at this point, see me for help. When you have done the assigned problems, you're in good shape.

Finally, before the exam, review as much as you can. At least read the end of chapter summaries (if you do not have time to reread the entire chapter) and your notes. Work the problems on an old exam or two, and if you have time, rework homework problems. (Old exams -- some with answers -- are available on the Chem 221 web site. Be aware that the topics covered on an old Exam #1 may not be exactly the same as those covered on your Exam #1, although there should be pretty good correspondence -- likewise for exams 2, 3, and 4.) If there are questions you cannot answer, review the germane material, and if you don't understand it, see me.

You mentioned remembering things that are important. How do I know what is important?

If you can do the homework problems without looking back at the text, you have remembered the important things. If you cannot do that, you have not (or are not able to combine what you have remembered in a useful way). Likewise, with regard to the old exams that are available in the library.  (This course does evolve over time so you may encounter a few questions on old exams that relate to material that is not being covered this semester.)

You mentioned asking you questions about things I don't understand. I can see that this could be helpful, but I don't like to look ignorant.

I understand. None of us likes to appear ignorant. But it is a paradox; if you were not ignorant of organic chemistry, there would be little point in your taking this course. In any event, you might keep in mind the following sage advice:

He who knows, and knows that he knows, is wise; follow him.
He who knows, and does not know that his knows, is asleep; awaken him.
He who does not know, and knows that he does not know, is ignorant; teach him.
[My job; this is what I get paid to do.]
He who does not know, and does not know that he does not know, is a fool; shun him.
[If you keep your ignorance a secret until the exam --- at which point it will be obvious --- you wind up in this category by default, even if you really belong among the ignorant. Would you rather be considered ignorant or a fool?]

I've heard people say that this is a "memory course." In other words, to do well, all you have to do is memorize a lot of facts. Care to comment?

OK. You do have to remember a lot of material. If you have a really good memory and you just remember fact after fact, you might get a B in the course. To really master the course, however, you have to understand the material so you can apply it to new situations. In other words, you have to be able to be synthetic and analytical in your thinking. Ideally, you should also be able to think critically.

One thing that you will need to do in order to master the material is to relate new facts and concepts to those you already know. This is something that I try to emphasize in class to a greater extent than is done in your text. I cannot cover all the material that is in your text in lectures --- there is not enough time. But I do try to relate things. So when I say something like, "This is very similar to the first step in the mechanism of electrophilic addition," don't let that comment slide by because electrophilic addition was covered on the last exam. I am pointing out the connection so you will begin to see the patterns that exist in the subject. And you should do the same as you study: try to relate what you are learning to what you already know. If you do this, learing the new material will be easier and more interesting.

What do you think about study-groups?

I think, properly used, they can be effective for some people. They are not a shortcut to success, however. YOU still have to put in a lot of effort to learn the material --- freeloaders neither contribute to nor derive much benefit from participation in such groups.

My view of it is that one would need to master much of the material before the study group would be helpful. When everyone in the group is at this stage, discussion of topics that are not well understood by one or more members of the group is likely to be helpful, as is going over difficult problems. The upside of the study-group is that if one of the group members understands a topic that others do not, the remaining members have an educational opportunity. The downside is that a situation can develop where the blind are leading the blind --- one person THINKS he understands the topic, but does not, and misleads the rest of the group. In this regard, I would certainly be willing to meet with a group to answer questions.

The bottom line here is: if it works for you, do it; if it does not, don't.

Are you aware of any pitfalls in terms of taking the exams?

I try to provide sufficient time so if you know the material you will have enough time to think and answer all the questions. Consequently, you have the time to read the questions carefully. Do so.

When you're answering a multiple choice question, it is usually best to try to arrive at the answer yourself, then select one of the choices. Don't expect one of the choices to jump off the page and shout at you, "I'm the right answer." I've been in this business for a long time and I'm pretty good at selecting plausible foils; sometimes, I can even make one of the foils jump off the page and shout, "I'm the right answer." But, if you have already arrived at the right answer, you will be in a position to foil such foils. [In cases where you are unsure of an answer, it may be possible for you to eliminate some of the foils. In cases like this, you should, of course, do just that and make your best guess among the remaining choices. There is no penality for guessing; you get the same credit (none) for unanswered and incorrectly answered questions.]

The first exam in Chem 221 includes a substantial amount of material that is more or less a review of general chemistry and does not include much about reactions, mechanisms, stereochemistry, and synthesis --- things that form the core of organic chemistry. Consequently, it is considerably easier than the ensuing exams. The second exam in 221 is probably a little easier than the ones that follow it. Don't be lulled into a false sense of security by good results on the first and/or second exams and slack off. If you do, you're likely to be rudely surprised by the third.

What do you think is the single most important thing for me to do in terms of studying and what is the single most important thing not to do?

The most important thing to do is put your pencil to the paper. Of course, you have to read the text and your notes. But some make the mistake of more or less stopping at that point. They have gained passive recognition and think they know the material. Close the book and write down what you think you know. WORK THE PROBLEMS!

Don't fall behind. Keep up with the work. Chem 221 and 322 are fast paced courses and you can fall behind very quickly. Keep moving, like the little guy on the left below, or you will wind up like the unhappy individual on the right.

Good luck!