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Organic chemistry
As you begin your study of organic chemistry, you might feel overwhelmed by the number
of compounds, names, reactions, and mechanisms that confront you. You might even wonder
whether you can learn all this material in a single year. The most important function of
a textbook is to organize the material to show that most of organic chemistry consists of a
few basic principles and many extensions and applications of these principles. Relatively little
memorization is required if you grasp the major concepts and develop flexibility in applying
those concepts. Frankly, I have a poor memory, and I hate memorizing lists of information.
I don’t remember the specifics of most of the reactions and mechanisms in this book, but
I can work them out by remembering a few basic principles, such as “alcohol dehydrations
usually go by E1 mechanisms.”
Still, you’ll have to learn some facts and fundamental principles to serve as the working
“vocabulary” of each chapter. As a student, I learned this the hard way when I made a
D on my second organic chemistry exam. I thought organic would be like general chemistry,
where I could memorize a couple of equations and fake my way through the exams. For
example, in the ideal gas chapter, I would memorize PV nRT, and I was good to go.
When I tried the same approach in organic, I got a D. We learn by making mistakes, and
I learned a lot in organic chemistry.
In writing this book, I’ve tried to point out a small number of important facts and
principles that should be learned to prepare for solving problems. For example, of the hundreds
of reaction mechanisms shown in this book, about 20 are the fundamental mechanistic
steps that combine into the longer, more complicated mechanisms. I’ve highlighted these
fundamental mechanisms in Key Mechanism boxes to alert you to their importance. Spectroscopy
is another area where a student might feel pressured to memorize hundreds of
facts, such as NMR chemical shifts and infrared vibration frequencies. I couldn’t do that,
so I’ve always gotten by with knowing about a dozen NMR chemical shifts and about a
dozen IR vibration frequencies, and knowing how they are affected by other influences.
I’ve listed those important infrared frequencies in Table 12-2 and the important NMR chemical
shifts in Table 13-3.
Don’t try to memorize your way through this course. It doesn’t work; you have to
know what’s going on so you can apply the material. Also, don’t think (like I did) that you
can get by without memorizing anything. Read the chapter, listen carefully to the lectures,
and work the problems. The problems will tell you whether or not you know the material.
If you can do the problems, you should do well on the exams. If you can’t do the problems,
you probably won’t be able to do the exams, either. If you keep having to look up an item
to do the problems, that item is a good one to learn.
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