CHM 233 : Fall 2008
General Organic Chemistry I
Department of Chemistry and Biochemistry
Ian R. Gould
PS D-109
965-7278
igould@asu.edu

Lectures
Office
Hours
Mon.  1:00-2:00 PM
Tues. 6:00-7:00 PM
Wed. 9:00-10:00 AM
Fri.  9:00-10:00 AM
Sat. 1:30-2:30 PM
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General Advice | Specific Suggestions | Advice From Students

General Advice

Organic chemistry is difficult because you are required both to be familiar with a number of facts, and also how to use and apply them. You can not get through this course just by memorizing, nor can you get through it by working everything out. You have to do some of both. You have to know the vocabulary of organic chemistry, and you also have to be able to use it in a reasoned way.

The only way to learn the material is to work problems! Do not get caught in the trap of thinking that you can study the material just by reading it. You have to study organic chemistry with a pencil and paper!

The textbook is an excellent resource, however, I often surprise students by telling them not to read the textbook! I don't really mean it, of course, I just want to draw their attention to the fact that reading the textbook should not be their primary study method. The problem with the textbook is that it is easy to read, it has nicely colored diagrams, everything makes sense, the concepts look familiar. However, it lulls you into a false sense of security. As you read it, you think that you know the material. However, understanding the material is very different from being able to do organic chemistry problems. On the tests, you aren't asked whether you read and understood the textbook, you are asked to solve problems you have never seen before.

Here is a suggested study strategy:

Start with the notes. They are shorter than the textbook, and summarize what you are expected to know. Flip through them and make a summary of the basic topics (e.g. reaction energy diagrams, meso compounds, preparation of alcohols etc). Look at this list and if there is anything that you know you really don't know, then read the notes related to that part (only). If you still don't understand, then go to the textbook to get a different explanation. Just read the part you don't understand and then return to your summary. Then go to the problems in the textbook, or other assigned problems. For each problem you should recognize which of the basic topics is being tested. If you get a problem wrong and you don't understand it, then return to the notes (and the book if necessary). This way you use problem-solving to tell you what you don't know, you don't waste time reading material that you don't need to.

You are not supposed to get all of the problems right! (first time). Doing a problem, geting it wrong, finding out why, trying it again later and getting it right is an important way that you learn. Make a note of all problems you get wrong, find out why you got them wrong, and return to them a few days later when you have (hopefully) forgotten the answers. Each problem you get right that you previously got wrong shows that you have learned something. It actually feels pretty good when you start to get the problems right, you build confidence and you know you are learning. Don't get discouraged and give up when you initially get the problems wrong and resort to just reading the textbook because it is easier. If you can't get any of the problems right, then you will need to start with a different way of studying, for example, by writing out an abbreviated form of the notes. You learn by writing, not by reading. If you don't understand something and the textbook doesn't help, then seek help from your instructor or a TA sooner rather than later!

Some of the problems you will do are easier than you will see on the tests, because you need to start getting the easy ones right before you can do the more difficult ones. Look at old tests to get a better idea of what will be expected of you. The tests will generally include problems with a range of difficulties, including some hard ones.

Do the problems honestly, without having the solution manual open in front of you. Don't do the following.... you try a problem, it takes you a long time, you eventually get it right. Then you look at the next problem, it looks hard... it looks like it will take a long time... it looks a bit like the one you just got right anyway... you really don't want to be doing this and would rather be somewhere else... you sneak a look at the solution manual, "Oh yeah, I would have got that one right!". No, you need to PROVE that you can get the problems 100% correct on your own.

Study in a group if it is truly helpful. However, if you work with someone who works fast, don't let them finish the problems for you then say to yourself "I would have got that". The fact is that you just didn't, and unless you can PROVE that you can do them on your own, you won't be able to do them on the test. If your study partner is slowing you down or is going too fast for you, then get a new one quickly, this isn't the time to worry about being a good friend!

HERE IS THE NUMBER 1 PROBLEM THAT MANY STUDENTS HAVE. A student comes to me saying "I understand this stuff, I can do it, why do I do badly on the tests?" They are understandably frustrated. I usually then ask what problems they did, then write one on the board in my office and ask them to solve it in front of me. Guess what, they usually can't, or they make a small but significant error that loses them points on the test! So now we learn that they can't do the problems on the test, or in my office. This often means that the student has "cheated" when doing the problems on their own (for instance by looking at the solution manual) even if they don't realize it themselves. If you do a problem and get it mostly right but make a small mistake, you can't tell yourself that you got it right and won't make the same mistake again, you have to tell yourself that you just got it WRONG, and that until you can go back and do that problem AGAIN perfectly, you will get it wrong on the test AND in my office. You need to make careful note of everything you get even a bit wrong, and don't let yourself think that you know it until you can prove to yourself that you can get it right, 100%. YOU HAVE TO ELIMINATE THE SMALL ERRORS TO DO WELL IN ORGANIC!

Another difficulty in doing problems is that they are given "in context". When you see a question on a test you aren't told that it is from Chapter X and on subject Y. When you do problems in Chapter 5 in the book you know they are stereochemistry problems (or whatever), and anyway the previous question was a stereochemistry problem, and so will the next one etc. Furthermore, there is often something on the page that you can't help looking at that helps you do the problem in the book. When you work problems, try writing the question down on a blank piece of paper, then close the book. You will then have to do a question as it appears on a test, there will be nothing else on the page to help you. If you can do the questions that way, then you should be able to do them on the test.

Many people say they get "test anxiety". Here is a possible cure that I know has worked for other students because they TOLD me it did! If you can prove to yourself that you can do problems honestly, before the test, as described above, then you will NOT be as anxious! You may even look forward to the test because you know that you know the material. If you know you can't do the book problems and you haven't tried them more than once, then of course you will be anxious during the test. I find that a lot of "test anxiety" is a result of being overwhelmed and not properly knowing the material. Try to study the way that I suggest, convince yourself that you CAN do the problems, then your confidence will build and your anxiety should diminish.

You have to test yourself before I test you. You should go into each test knowing how well you are going to do. Test yourself to see if you know reagents, mechanisms and reaction products etc perfectly. When studying, if you find something you don't know, make a note of it and made sure that you practice it again next study period.

I have observed that people who carry heavy course loads or work many hours outside school tend to be disappointed in their performance in Organic. There isn't much that I can do about that. Importantly, most people also tend to maintain their positions in class throughout the semester. Do well on the first test and you tend to do well on the rest of the midtems and on the final. Unfortunately, the reverse is also, look at the plots below as a typical example. If you want to do well you will need to start working straight away, if you leave it late for the first test you WILL be disappointed.

Unfortunately, I have also found that some people just aren't destined to do well in Organic, no matter how hard they and I try together (this is certainly an important contributing factor to the plots above), and you may have to accept that you are one of them. Not everybody is good at everything, I certainly am not! I am sure there are many coures taught at ASU that I would not get an A in.

Don't let reading this give you the wrong impression of Organic Chemistry, it really isn't all bad! Many people do very well in my courses and tell me that they really enjoyed them. You never know, this could be you!

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Specific Suggestions

1. A SPECIFIC SUGGESTED STRATEGY.A suggested study strategy was suggested above. It is important that whatever strategy you use, it must be very systematic and rigorous, you need to know exactly what you are supposed to know, and you need a method to determine whether you know it yet. That part of the strategy that deals getting these basics out of the way (what are you supposed to know etc) is detailed in the following small movies (click the links). They refer to second semester material, but if you are a first semester student the principles should be obvious.

Part 1 : The Reactions | Part 2 : The Mechanisms | Part 3 : The Concepts

Of course, these suggestions relate only to how to deal with the notes. As you have now heard too many times, probably, your PRIMARY study tool is WORKING PROBLEMS!

2. MEMORIZATION. In this course you WILL have to do SOME memorizing. There is nothing wrong with some memorization, it is a part of any academic study. A course that was all memorization would obviously be boring, but organic isn't like this, however, you can't work everything out in organic. The usual statement at this point is that there is a vocabulary associated with the organic chemistry language that we all need to know to be able to communicate properly. It sounds a bit trite, but it is actually true!

Let's look at a specific example to see how to handle the memorization aspect of studying. One of the first things you will have to learn are the functional groups. So, how are you going to do this? My suggestion is not to memorize them (yet!). What I mean by this is if there is something you need to memorize, DON'T START by memorizing the facts first, instead, start by working problems that USE the information.

In this case, you would solve as many problems as you can that require you to identify functional groups, e.g. click HERE, or in the textbook. Work most of these problems with your functional notes open in front of you (otherwise you wouldn't be able to do them). In this way you learn how to solve these kinds of problems, you learn to see the functional groups in different contexts and you practice what you will be asked to do on a test

In the course of doing this you will find that you have learned quite a few of the functional groups without having to memorize them. If you try to memorize the facts before doing the problems it will be like memorizing names out of a telephone book, you won't see the point, it will be boring, and because it is not in context, you won't remember them as well. By doing problems first you will see the context, you will do some of the memorization "by default".

There will still be a few details that you still don't know. These you may have to memorize before a test. This next part may sound a but shocking, but I would leave the memorization part until just before the test. I don't actually care if you "cram" some of the functional groups for the test because even if you forget them immediately afterwards, I know that you will learn them all eventually over the course of this semester just by using them. We rarely ask you to memorize something that you aren't going to use again and again.

So, how to do the final memorization part? You have to be both systematic and also rigorous about this. There is a method that I think will be useful to a lot of people. I know that it is useful because it worked for me when I took organic chemistry many years ago! It is most easily explained in terns of a movie (click the link).

A Strategy For Memorization (warning, large movie file!)

 

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What Some Former Students Suggest
John Merolo : CHM 331, Fall 2003

The most important aspect to studying I've found for this class is to DO PROBLEMS. And by doing problems, I don't mean the night before. The problem sets and practice tests (Dr. Gould) gave were invaulable, along with the weekly work. The only way I was able to grasp the retrosynthesis problems was to work out every every one I could find, every night for a week straight. By the time the final came around, I was well prepared to see new ones.

Also, I found that flashcards helped with the reactions. Even just copying the reaction sheet (Dr. Gould) gave us was enough to help me recognize reactants and products. It also helped quite a bit to write out the mechanisms for the important reactions. It all boiled down to practice.

Hoang Tran : CHM 331, Fall 2003

1) Go to class AS MUCH AS POSSIBLE, copying notes from a friend does not work. Only by watching and listening in class will you understand.
2) Make a note of anything that doesn't make sense in class then read that section in the textbook.
3) Especially for the first test, do the book problems to get a feel for how 331 works. Gould's approach is very conceptual but if you do the book's not-as-conceptual problems you will learning from another angle. Take the test and see how well you have honestly studied and prepared. If you did really well, then (honestly now) lessen your investment time in OCHEM, or keep it the same (cause the class gets harder and harder). If you scored poorly, then it probably correlates with how much time you invested into doing the practice problems.
4) Problem sets are worth more than their weight in Gold! Download the problem sets right away and start working on them. They indicate the type of concepts and relationships Dr. Gould wants you to know.
5) Read Dr. Gould's study tips, and his thoughts on how to 'honestly' do O-Chem (don't cheat yourself into thinking you know O-chem if you don't).
6) Study with friends or lab partners, sometimes a different perspective helps.
You must invest time into this class if you want to succeed. From my experience AND talking to many other students: your test scores DIRECTLY correlate with how much time you spend honestly doing O-Chem before the test. There's almost no way around it. You just need practice with it to understand it.

Dave Bennett : CHM 331, Fall 2003

The thing that helped me the most in your class was going to every lecture and review session. Before each test, I would take all three previous tests and time myself. Then I would go through and correct the test, and the one I missed the most on, I would do again. I used your notes to make flashcards, this helped a lot.

Lindsey Trutter : CHM 331, Fall 2003

Always go to class and try to do the weekly reading before the lectures for that week starts. That way you can develop an understanding and avoid going into lecture and being confused.

Rowena Cheung : CHM 332, Spring 2003

I've learned that when students like myself start off learning the rxns, they think that they've got to memorize what this reagent does... The thing you had stressed about is to NOT memorize... Maybe here's a method to help?
I would take the retrosynthesis problems. In the Forward direction, I would cover up the product formed by the first reagent. Then, I would attempt to draw the product from the reagent given. I would uncover, look at the molecule, and remember , okay.. this reagent does this..." copy the reagent once. Then go to the next step and repeat the same thing. As I come across the same reagents again and again... I will begin to learn its reactions. Then, I would wait a few days and do the problem again without peeking at the reagents...
It's kinda like math. You've got to learn the (basics) forward direction, for example 1 + 1 = 2. Then, you can do the (algebra) in between reactions, for example 3x + 2 = 14.

Lubna Ahmad : CHM 332, Spring 2003

1. Print out all of the notes beforehand!
2. Come a few minutes early to class and read over the notes from the lecture before. It's amazing how much more sense they make when you look at them holistically.
3. Print out handouts before you cover the reactions. Check them off as you cover them. The handouts present a more succinct version, which is often helpful. (this semester there won't be handouts, the reaction summaries at the end of each Chapter of notes will serve the same purpose, i.r.g.) 4. Keep the handouts (reaction summaries, i.r.g.) accessible to you while you do the book problems so that you learn the reagents, but do the problem set completely without them. If you don't use the book at all, then print out the practice problems that Dr. Gould has in the "Weekly Work" section and use those to learn the reagents/conditions. 6. While working through the problem set, I usually made a sheet that consisted of the following:
* Trends in the ranking sections
* Reagents that I regularly missed
* Previous reagents that I had forgotten
* Other notes

Click here to see an example of such a sheet. It might be useful for students to collate these over the course of the semester so that they can identify their individual weaknesses.

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