Study Tips '09

(updated version of post from Aug 20, 2008)

An idiosyncratic assortment of suggestions and observations based on 23+ years of teaching.

  • Studying is a personal experience. Flexibility and patience are essential.
  • It’s all problem-solving
  • Practically every problem uses experimental observations as a point of departure. You will have to learn these observations.
  • Get to know your book.
  • Get to know me.
  • You will get frustrated at times. Hang a large “Emergency Kindness” button over your desk and use it.

Studying is a personal experience.

Doing X works for me, but I can’t say whether it will work for you. The personal nature of learning also refers to the fact that something actually happens to your “person”, that is, your body, when you learn. Biochemical and physiological changes must occur in your brain, and your ability to make these changes is limited by your brain’s operating environment (biochemical, neurological, psychological) and by the time you allow for these changes to occur. Take care of yourself. Start your studies sooner rather than later. Be patient with yourself.

EXPERIENCE – The only way to find out is to try different study techniques and pay attention to what happens. Flexibility is mandatory.

It’s all problem-solving. 201 and 202 are based on
problem-solving, showing that you can apply what you have learned to new
situations. Some thoughts on problem-solving:

1. It is a good way to learn new material. I preach
the value of memorization (see below), but it has its limits. Memorization entails rehearsing the same thing over and over again.
There is no application. There is no context. There is no novelty. Problem-solving, by contrast, brings
other essential information skills (retrieval,
selection, combination, and application) into the picture. Each problem provides a new context for the information you are trying to learn. Use memorization and problem-solving to learn material.

2. Practice! Problem-solving is difficult
and slow because several skills (retrieval-selection-combination-application) must be performed correctly for the overall
process to succeed. Practice is the only way I know to make difficult
things easier and to make slow things faster. Practice actually reshapes your brain’s environment so that you become a more effective problem-solver.

3. Pay attention to how you feel. Are there problems that make you uncomfortable? (Some problems certainly make me
uncomfortable.) If they do, you might be reluctant to do as much
problem-solving as you should. This is a natural response. You can be a
spectator in lecture. Reading is fairly passive
too. Problem-solving pushes you to be active. If
you are going to solve a problem, you have no choice but to create
something (“an answer”) that doesn’t yet exist. So if problem-solving
makes you feel uncomfortable, that’s a natural and valid response, but
realize that these feelings may get in the way of practice and practice will, over time, reduce the intensity of any
unpleasant feelings.

4. Repetition + variation. Once you learn how to solve a
particular type of problem, move on. Change the degree of difficulty. Figure out which problems you can do reliably,
easily, and quickly, and which are still problematic.

5. Whenever you feel stuck for whatever reason (intellectual, emotional), come see me.

6. Base your practice on your textbook. This is simply a matter of supply and demand. Practice demands lots of problems and your textbook supplies hundreds of them. By comparison, I will write only a few dozen homework + exam problems during the entire semester.

7. Think it? Draw it!
85% or more of our problems require drawings as answers. But drawings are not just what you produce at the end, they are also what you use in the middle of the problem-solving process.

It’s true that you can sometimes work a problem in your head, but let’s not get stuck up about this. Most problems are too complicated to be worked that way. Consider, when you work a chemistry
problem, you need to juggle several ideas (molecular formulas, reagents,
alternative answers) in your short-term working memory. This
memory can hold only 5-7 items at a time (and only with intense
effort). When your mind wanders, or you start to manipulate one or two items
in your short-term memory, the rest of your short-term memory gets
flushed. If you’re relying on your memory alone, you won’t get very far before you’ve forgotten almost everything you need to solve the problem.

How do you get around this? By drawing. Once you make a
drawing, the information in the drawing no longer needs to be kept in

Here is my standard recommended approach for working most
problems (based on the way I was taught to do algebra problems):

  • First drawing: the information (formulas, reagents, etc.) given to you in the problem.
  • Second drawing: one change in this information that you think might bring you closer to an answer (no erasing; make a new drawing)
  • Third drawing: the next change (don’t erase!)
  • Repeat as needed until you get to the final drawing. Organize your drawings logically on the page (in algebra, we would put each new equation under the previous one). Note: almost all answers to organic chemistry problems will be drawings.

8. Learn to draw and draw to learn. If you write facts over and over, you will remember these facts. If you draw a formula over and over, you will remember how it is put together and its shape. Drawing, which I previously advertised as a tool for keeping track of information, is also a tool for inserting information into your memory. The authors of a textbook that we no longer use [Solomons & Fryhle} advised students: “Organic chemistry is best assimilated through the fingertips.”

9. A solutions manual is a wonderful/dangerous thing.

I hate sitting in front of a difficult problem when I know the answer
is right over there in the solutions manual. If I get stuck, I like to
peek at the answer. Bad idea, you say? Not necessarily, but depending on how you do this, it could
a bad habit. If you see that you can only solve problems by peeking, you haven’t really learned to solve problems.

Practically every problem uses experimental observations as a point of departure. You will have to learn these observations.

You have probably heard that organic chemistry is “all memorization”, and while I could quibble with some aspects of this statement, I can’t really deny a basic truth: successful students do a lot of memorizing. Why is this necessary?

The simple answer is that chemical phenomena are incredibly complicated and cannot be deduced from first principles. To see this, try answering this “simple” question: is methylamine, CH3NH2, a liquid or a gas under standard conditions?

Give up? This problem is impossible to solve from first principles, that is, by working your way from the properties of individual CH3NH2 molecules to the properties of a large ensemble of molecules at room temperature and atmospheric pressure. The problem is not impossible to solve, however, if you approach it the right way.

If you know that ammonia, NH3, is a gas (this must be memorized – you can’t deduce it from first principles) and then you recognize that NH3 makes more hydrogen bonds than CH3NH2, you might realize that CH3NH2 is a less-sticky molecule than NH3 and is probably a gas too.

Notice that some reasoning is required (you must compare NH3 and CH3NH2), but the key “point of departure” is an experimental observation (NH3 is a gas), a raw fact. You can learn facts by memorization, but memorization is not the only way, or even necessarily the best way, to learn experimental observations. Problem-solving is another useful tool for learning the essential facts of organic chemistry (see above). However, regardless of the method(s) you use, you will need to learn many experimental observations.

Get to know your book. Only one (fat heavy) book is used for all of 201-202.

  • Inside covers. The front cover contains
    a lovely chart of functional groups. These are the basic nuggets that we use to process structural formulas so this information is really useful. The back cover contains the periodic table. ‘Nuff said.
  • Appendices and Index. Wikipedia is great (truly!), but if your book is in your bag, you don’t need tget online. A great deal of frequently used data are presented in 15 pages of appendices. Practically everything else you need is somewhere in your book. The best way to find it? Look it up in the 38 page index.
  • Study Guide Links. This feature connects your textbook to your study guide. A small “book” icon in the margin of your text alerts you to the presence of additional material in the study guide.
  • Key Ideas lists. At the end of every chapter is a list of the most important ideas found in that chapter.
  • Concept maps. Your book doesn’t contain any concept maps (aka ‘mind maps’), but why not make your own? They are a great way to take notes and see relationships between concepts. Some teachers believe that
    drawing a concept map is one of the most powerful learning tools available. Check out this cool web site for some extra help and let me know what you think.
  • Problems. A huge slice of your book is devoted to problems. Study problems contain solutions right after the problem. Try to work them before you read the solution. Regular problems are scattered throughout the text and provide a way to check on your understanding of the material you read. Additional problems are located at the end of each chapter for more problem-solving practice. You should plan on doing a significant number of additional problems as part of your habitual study pattern.
  • Self-adhesive flags.
    Your book is huge. Finding information can be tedious. You can make
    this easier by pasting little self-adhesive flags on key pages. It also
    helps to write short topic labels on the flags.
  • Study Guide & Solutions Manual. An important add-on for your textbook. What does it contain? Chapter summaries. Glossaries. Reaction summaries. Solutions to many (but not all) problems. Study guide links amplify on particularly confusing parts of the text. Further Explorations are there to introduce material that goes beyond the basics of organic chemistry.

Get to know me. You don’t have to wait for an emergency. Although a lot of the
routine stuff I do (leading classes, writing, grading, etc.) is pretty
time-consuming, I would like to spend several hours each week meeting with
students (but perhaps not several hours with just one student).

Please come by my office and say “hi”. You don’t need an excuse. You can even say “hi” if we have already said “hi” to each other in conference or lab.

I will keep regular office hours, but I am also
available outside of those hours. Some students like to drop in
unannounced, others like to set up appointments. I can meet with individuals and with small groups.
Many conversations are tutoring sessions, but sometimes we just chat.
There is really no set pattern. The only constant is that I would really like to meet
each of you, and if help is needed, provide it.

Since one of the ways to arrange a meeting is for me to send you a note, I’m going send you a note right now.

To: All students enrolled in Chem 201, Fall 2009

From: Alan (8/09)

Please come see me.

Students who respond to this note (you must say “I came because I saw your note”) will be treated by me to one free Paradox beverage of their choice. I kid you not.

OK, another thing that you might want to know about me: how I teach.
I’m a big believer in the written word – books, handouts, web pages –
and this affects how I teach. For example, I write a lot. I also expect you to read a lot. You are going to be responsible for practically everything written in chapters 1-14 of your textbook.

believe in the spoken word too. Direct
human-human contact is an extraordinary experience. Unfortunately, verbal communication seems like a less
reliable way to pass along information, especially in quantity. If a speaker stumbles or a
listener’s attention wanders, something gets lost. I don’t
try for complete coverage of the material when I lecture. Instead, my
lectures are intended to: 

  • illustrate how a chemist (me) talks, draws, and weaves together experimental observations and theories
  • introduce you to the major characters in each chapter so that the material is easier to read
  • occasionally supplement book material with additional material that I consider important
  • provide a practice space where you can draw, think, and maybe converse, about organic chemistry

I believe “teacher” and “student” are only administrative
labels. During our time together, we will all learn, we will all teach,
and we will all be changed, hopefully for the better. You will teach me
and I will learn from you. One way this happens is when I gaze out over
the sea of faces in lecture. Much better are one-on-one conversations.
I am also hoping that you will add comments and questions to this blog.
I should add that
positive and negative feedback are both useful.

Hang a large “Emergency Kindness” button over your desk and use it.

Are you one of those smart, hard-working people who demand a lot from
themselves and push themselves to excel? There’s a good chance you are.

Suppose one of the following happens to you:

  • you sleep through your alarm
  • you fall behind on your daily to-do list
  • you don’t finish
    all the pages in your reading
  • you lose your laptop
  • you get stuck on a
    homework problem
  • you have an uncomfortable “silent” moment in
    conference when responding to an instructor’s question
  • you spill half of the liquid in your beaker on the lab floor
  • you draw a total “blank” on a 20 point exam problem

Would any of these things upset you? For how long? What would be your physical response? Would your heart start pumping? Would your stomach churn? What would be your emotional response? Would you beat yourself up emotionally? “Why am I so dumb?” “Why can’t I get my work done?” Would you turn yourself into a victim? “Why do these things always happen to me?” “Why does my prof assign these ridiculous problems?”

These are all normal responses, but they aren’t good ones. Since it is inevitable that a poor performance and a high expectation will eventually collide, we need to find some way to deal with life’s upsets that doesn’t involve turning ourselves into hyper-stressed Type A maniacs.

Here’s my advice: problems are real, but not one problem can be
made better by smacking yourself (or someone else) around. You would never kick a person
with a broken leg, so why would you respond to the insults and
injuries of life by mentally kicking yourself? When your spirit hurts,
pay attention to it. Tend to it the same way you would tenderly take care of
a broken leg. Be kind to yourself.

If you think it will help, hang a red ’emergency kindness’ button over your desk to remind you that there is another way to behave. Press it whenever the situation calls for some emergency kindness. You deserve it.

Added Sept 1, 2008: The NY Times (Aug 27, 2008, Health) carried an article about Psych Central’s “Online College Survival Guide“.
This is a collection of essays with advice on diverse topics ranging
from time management, stress, procrastination to getting a passport and
dealing with loneliness.

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2 Responses to Study Tips '09

  1. Alan Shusterman says:


    Seriously. At the risk of going overboard with advice, put this note in your day planner for Sunday, Sept 27: “read Chem 201 study tips again”.

  2. Josh Katz says:

    I think a lot of the pedagogical advice would have been quite helpful last year with Hum.

Comments are closed.