Study Tips

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

  • Studying is a personal experience. To stay successful, it needs to evolve.
  • It’s all problem-solving
  • Get to know your book
  • Get to know me
  • Install a big red “Emergency Kindness” button on your wall

Studying is a personal experience. To stay successful, it needs to evolve.

– although I find doing X works for me, I really can’t say whether it will work for you.

EXPERIENCE – the only way to find out what works and what doesn’t is to do things and pay attention to what happens.

EVOLVE – what works today might not work tomorrow (but it might the day after)

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

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

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 slow things faster.

3. Pay attention to how you feel. Do some problems make you uncomfortable? (Some 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 problems during the entire semester.

7. Think it? Draw it!
If you are lucky, you will be able to solve some problems in your head,
but you won’t be able to rely on this. Fact: when you work a chemistry
problem, you need to keep several ideas (molecular formulas, reagents,
alternative answers) in your short-term working memory. Fact: this
memory can hold only 5-7 items at a time (and only with intense
effort). Fact: when your mind wanders or you start to manipulate items
in your short-term memory, the rest of your memory’s contents will get
flushed. So 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
memory. 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 (don’t erase, make a new drawing)
  • Third drawing: the next change (don’t erase!)
  • Repeat as needed until you get to the final drawing. (Note: almost all answers will be drawings.)

8. 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 it could
a bad habit. If you see that you can only solve problems by peeking, you haven’t really learned to solve problems.

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

  • Inside covers. The charts summarize some of the
    most-used information in the course. The front cover contains
    information on the most important reactions: acid-base (Ch. 3) and
    nucleophilic substitution/elimination (Ch. 6-7). The back cover
    contains charts for interpreting IR spectra (Ch. 2) and NMR spectra
    (Ch. 9).
  • Glossary + index. Tucked away in the back of the book are an amazingly detailed 13 page glossary and 28 page index. Try looking up Natural Products Chemistry and Green Chemistry.
  • Key Terms and Concepts. This list, located at the end of each chapter, contains all of the terminology that you should become acquainted with.
  • Concept maps.
    These maps, also located at the end of each chapter, are powerful tools
    for seeing relationships between ideas. Some teachers believe that
    students can benefit from making their own concept maps. If you would
    like to try this but need a little help, come see me. If you prefer
    expert help, check out this cool web site (note: mind map = concept map) and let me know what you think.
  • Problems? Exercises? The problems in your book are labeled several ways: study problem, review problem, exercise, problems, challenge problems, learning group problems. As I understand it, study problems
    show you a problem and a worked-out answer. In other words, these
    illustrate how a chemist works through a problem. The remaining
    problems are of varying difficulty and you should incorporate all of them into your problem-solving practice.
  • 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.
  • To The Student (p. xxxiv-xxxv). Your authors provide two pages of free sound advice. Notice Tip #4 – Write when you study. I can’t emphasize enough the importance of drawing formulas (and building models, Tip #8). At least 85% of the work you turn in will consist of formula drawings. Learn to draw and draw to learn. As Solomons and Fryhle put it, “Organic chemistry is best assimilated through the fingertips.”

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 hope to spend several hours each week meeting with
students, so please come by my office and say “hi”. You can do this
even if we have already said “hi” in conference or lab.

no set pattern for meetings. I have office hours, but I am also
available outside of those hours. Some students like to drop in
unannounced, others like to set up appointments, sometimes I contact
students I want to see. I 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 use this method right now.

To: All students enrolled in Chem 201, Fall 2008

From: Alan (8/08)

Please come see me. (Students who follow up on this invitation are entitled to one free Paradox beverage of their choice – my treat.)

I’m not kidding. This is a genuine invitation.

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 expect you to learn all of the material in your textbook
(at least, for the assigned chapters). Another consequence is I write a
lot. I am currently writing study guides for each of the chapters. The
guides will be posted online and will list all of the basic
skills/concepts that you should retain from each chapter. They will
also list textbook problems that practice these skills/concepts.

believe in the spoken word too, but mainly because I think direct
human-human contact is so valuable. Spoken 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.

Install a big red “Emergency Kindness” button on your wall.
Are you one of those smart, hard-working people who demand a lot from
themselves and push themselves to excel? I bet you are. You
probably wouldn’t be at Reed if you weren’t that type of person.

type of person can be brutally hard on
themselves when things don’t go well. That’s a problem because there
are a lot of ways in which things might not go well:
sleep through your alarm, fall behind on your to-do list, don’t finish
all the pages in your reading, lose your laptop, get stuck on a
homework problem, have an uncomfortable “silent” moment in
conference, spill half of the liquid in your beaker on the floor,
completely bomb a 20 point problem on a 100 point exam. These things
are just the uncomfortable facts of everyday Reed
College life. We all hope that they won’t happen, but when they do (and
they always do), they turn you into a smart, driven, high expectation
person with a problem.

So how do you handle these problems? What do you do when your life
and your expectations collide? If you are like most people, you probably beat up on yourself. Hard. I know this from personal experience. I have a very
hard time taking any of my advice regarding unrealistic expectations,
work habits, sleep patterns, etc., and there are many faculty just like

That said,
here’s my advice anyway: problems are real, but not one of them can be
made better by smacking yourself around. You wouldn’t kick a person
with a broken leg, so why should you respond to the insults and
injuries of life by mentally kicking yourself? When your spirit hurts,
pay attention to it and tend to it the same way you would take care of
a broken leg. Be kind to yourself. If you think it will help, paint a red ’emergency kindness’ button on your wall and press it as often and long as necessary.

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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One Response to Study Tips

  1. Michael Komansky says:

    Hi Dr.Shusterman,

    I am a pre-med student in New Jersey and happened upon your blog. Your work is greatly appreciated!
    Currently I am taking an Organic Reactions class at my college while I review for the MCAT. Your comments following the chapter reviews are helpful and entertaining (with footnotes). Don’t know if you hear it enough from your students, but…
    “Thank you”


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