Summer Suggestion #3 – Study Organic Chemistry

Organic chemistry is, despite what you may have heard, pretty much the same everywhere, whether MIT or Portland Community College. The courses that science majors and pre-meds take are 2 semesters (3 quarters) long and rely on a commercially produced textbook. There are about a dozen texts to choose from, and they all look pretty much the same: same physical size, same #chapters, same #pages, same content, and (usually) the same topic sequence. (Only the price tag changes!) If this similarity doesn’t persuade you, consider this, the American Chemical Society offers a standardized test for organic chemistry to college professors in order to test their students at the end of the year. (We don’t use this test, but I have no doubt that most of you would do well on it.)

When you think about this degree of standardization, you might guess that just about any college-level material you study will be helpful and you would be exactly right, but as I suggest below, a textbook might not be the best choice for summer work. Instead, I suggest that you find one of the “supplement” style books that I list and work with it instead. Notice that I say, “work,” and not “read.” That’s because all of the supplements are workbooks where you read a little and then do some problems. I think the following two paragraphs (quoted from To the Student in Pushing Electrons) says it best,

“I have only three instructions. First, supply an answer wherever a line appears under a blank space. The correct answer might be a word, a number, a structure, or some arrows. Second, don’t look up the correct answers until you have made a serious try at doing it yourself. Third if you plan to just look up the right answers and transcribe them, return the book and get your money back.

The program uses two effective learning devices: active involvement and repetition. You will participate actively in the learning process. Because so much of the academic experience consists of receiving information, it should be refreshing to work through a program using your own wits. You will see an example of an operation and then carry it out several times as the supporting material is gradually removed. The approach is methodical. Some of you will find that you can accelerate your trip through certain sections. But the program has been written in the hope that none of you will ever feel abandoned. Expect to spend a total of 10 to 14 hours to complete the program.”

4 Books To Consider:

  1. Organic Chemistry, 2e by T. Sorrell.
    1. Upsides: This is the Chem 201/2 textbook. It is inexpensive and nearly every chapter offers a few pages of biochemical applications. Cool! Another plus: all of the assigned readings (in sequence) are available on the Chem 201 Classes page. Reading the book is good practice for the reading/study you will have to do in the fall, and the book is loaded with practice problems, summary tables, and other helpful features.
    2. Downsides: The answers to the book’s problems are located in a separate book call the Solutions manual. Both the textbook and solutions manual are huge. Nice adornments for your dorm room, perhaps, but inconvenient to take to a coffee shop or the beach. Also, like all textbooks, this one contains a large number of details and asides that, while essential in the fall, are distractions in the summer.
    3. Bottom-line: Getting familiar with your textbook can only help, but this may be biting off too much for a summer task. One of the following “supplement” books might be a better summer companion.
  2. Organic Chemistry I as a Second Language (also listed as Second Language: Organic Chemistry I) by David R. Klein. This can be used for summer prep and also as a supplement throughout the fall.
    1. Upsides: Paperback (just under 400 pages) with answers in the book. The book is written in an informal style that makes it feel like light reading (to a point). The topics covered by volume I parallel those in Chem 201 fairly closely.
    2. Downsides: Obviously, a short book skips material that we will cover in 201. And, while you should learn the author’s explanations/approaches/tricks, you must also be prepared to revise your thinking/drawing habits in the fall because I will provide my own views and instructions.
    3. Bottom-line: This is probably the most comprehensive summer prep book that I can recommend. All editions, new or used, should be fine. Work with Volume I. You do not need Volume II.
  3. Pushing Electrons: A Guide for Students of Organic Chemistry, 2e by Daniel P. Weeks. (This is the book that I quoted from above.)
    1. Upsides: Paperback with answers in the book. Much, much shorter than “Second Language” (about 160 pages). Very manageable time investment. (“Expect to spend a total of 10 to 14 hours to complete the program.”)
    2. Downside: The book’s brevity is its chief asset and liability. It consists of only three sections: Lewis Structures, Resonance Structures, Mechanisms. And you will no doubt need to adjust some of your thinking/drawing habits in the fall.
    3. Bottom-line: If you are unsure of how much time you have for your summer prep project, this might be the best way to go. It is the shortest book of all, it reviews at least two key topics from 101/102, and it gets you doing (some of the) things that organic chemists do. Both editions should be fine.
  4. Arrow Pushing Organic Chemistry: An EASY Approach to UNDERSTANDING Reaction Mechanisms by Daniel E. Levy. Note: the italics in the title were supplied by the author, not me.
    1. Upsides: Paperback (just under 300 pages) with answers in the book. Significantly shorter than the “Second Language” book, but covers many more topics than the “Pushing Electrons” book. For example, this book contains the occasional drawing of orbitals, whereas “Pushing Electrons” does not.
    2. Downsides: The writing here is much more formal than what you will find in “Second Language”. And, as with the other supplements, you will need to revise some of your thinking/drawing habits in the fall.
    3. Bottom-line: Don’t be fooled by the similarity in titles for #3 and #4, “Pushing Electrons” vs. “Arrow Pushing”. These books are quite different.
  5. (added 8 Aug 2019) Preparation for Organic Chemistry by I. David Reingold.
    1. Upsides: Kindle-friendly ($9.99). Manageable content that is explicitly designed for the summer before taking organic. Just 9 chapters (250 pages text + problems).
    2. Downsides: This book is more of a voyage into the sections of general chemistry that are relevant to organic chemistry, rather than a voyage into organic itself. This is supported by the book’s Table of Contents (the only part I have seen) which looks a lot like my list of important Chem 101/102 topics. See Suggestion #1 – Review key topics from Chem 101/102.
    3. Bottom-line: If you are looking for a deep dive into, or just more exposure to, the “new” topics that organic chemistry will introduce, then this isn’t your book because it will cover only the first couple weeks of Chem 201. On the other hand, it could be just the summer preparation you need?

Decisions, decisions. If you have access to only one book (even the textbook), use what you have. If you have access to 2 or 3 supplements, then here’s a way to decide. First, think about time. If you are looking for a small time commitment, choose “Pushing Electrons”. Second, if you are ready to commit to a more substantial summer prep, consider writing style. Read 3-4 pages of “Second Language” and “Arrow Pushing”. Which style meets your needs? Go with that book!

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