Summary of Curved Arrow Press Activities

I received the following letter and I wanted to respond.


I recently purchased the Guide to Organic Chemistry Mechanisms With Conventional Curved Arrows. I will be taking my first organic chemistry course this fall and your guide looks as if it will very well complement my understanding as I move through the course. I have not found any individual reviews online from other students who have used your guides, so this is a bit of a blind trial for myself. I will be sure to let you and other students know how it has served me throughout the year. However, the confidence and detail that you’ve written on your site about how it has helped students is assuring.


By way of review, I wrote the books by taking the mechanism sheets I was using in my classes, standardized them, and published them in the current books. I was using Paula Bruice’s organic chemistry text and they were organized roughly around this book. I added a reasonably comprehensive table of contents and index with the objective to enable students using any book to find relevant reactions.

I had also invited professors to adopt the book as an ancillary to their courses. I gave a talk about using the book at a Middle Atlantic Region Meeting of the American Chemical Society. I had also hoped that I could have gotten a professor to join in seeking a National Science Foundation grant for a new methodology of teaching organic chemistry. I thought the excellent results I had in my classes would have sparked interest and funding. Alas, the responses have been underwhelming.

I was also aware that the book and my teaching was rather avant garde. I had adopted a different usage for curved arrows in order to attain a high level of consistency and remove ambiguity. I tried to soften some of the novel ideas noted or indirectly applied in reaction mechanisms.

None the less, I felt I needed to complete another title that I have been thinking about, researching, and drafting, “The Nature of the Chemical Bond – Revisited”. There are a number of chemical issues that are inconsistent, notably electronegativity. I had given a talk at an ACS meeting in 2004 about “The Enigma of Electronegativity”. I based this talk upon a review of Linus Pauling’s original ACS paper in which he introduced his electronegativity theory. Although electronegativity notion is clever, it is also not good science. Even Pauling notes that his principle contradicts expected chemical behavior.

Electronegativity has been a major hurdle to explain. It is easy to contradict, every organic chemistry book contradicts the principle with statements as “carbon is a better electron donor than hydrogen” or “iodide is a better leaving group than fluoride”. Pointing out the obvious hasn’t negated the concept. Now, I believe I have succeeded in providing a good scientific explanation to the data Pauling used for creating his electronegativity theory. I am giving a paper at the American Chemical Society Meeting in Philadelphia in August, 2012.

My time writing this book has taken time away from updating A Guide to Organic Chemistry Mechanisms. This is what I perceive as its weakness. When I taught a class in which Wade was the book being used, I found it difficult to match reactions from Wade with my book. For my purposes, Wade was poorly organized. Although I had been told that Wade had been adopted because of its mechanistic strengths, I thought this was its weakness. Many mechanisms were skipped when introduced. As a consequence, students may not have known a mechanism even if the reaction was covered in a chapter. (The mechanism may be covered, simply in another chapter.)

This is what I did not like about this. First, it indicates to students that mechanisms are optional. In my class, I suggested to students that they only had to know the mechanism of reactions they wanted to give an answer to on a test. Because mechanisms build upon other mechanisms, skipping a mechanism creates a gap in understanding. It is easier to add a variation to a mechanism you already know. The more mechanisms you know, the easier it is to add more to your knowledge. The second problem was I spent a lot of time searching for mechanisms and assigning problems associated with them. In the end, I simply guided my class around A Guide to Organic Chemistry Mechanisms and found sections of Wade that I assigned for reading and problems.

I discovered that even though I tried to make the table of contents and index to be as helpful as possible, the reality for many students is they cannot recognize reactions from keywords or titles. They need a specific assignment. A Guide to Organic Chemistry Mechanisms would probably be a lot more popular if there were versions of it matching their textbooks.

Therein lies the challenge. I really would like to extend our knowledge of chemistry. I would like the mechanisms as I have written them to be generally accepted because they match the actual electron movements much better than some of the simplifications offered in other textbooks. In order to achieve that, I need to explain a different model for atomic structure. I need to convince younger chemists that atomic theory should also be consistent with the rules of physics. That many chemical principles are better explained with the inverse square law. The inconsistencies of electronegativity theory become readily understandable by the inverse square law.

Other aspects of this prospective book become more difficult to summarize. I ask a reader to be open minded, to think, to reason, to ask whether the assumptions having been made are correct. I challenge some conclusions that have led to our current model of atomic structure. However, this is a challenging task. I am making something of a rimshot. I agree with most of what we know, but knowledge is like a knitted afghan, you cannot pull out one knot without affecting the rest. I am trying to open a new door. In most some cases, no changes in theory or explanation are required. In other cases, I hope chemists can simply adopt new alternatives. Chemists have competing molecular orbital and chemical bond theories. I hope that I can provide a satisfactory model in which these two theories may be joined.

Back to the question at hand, I consider my book to be superior as a learning tool. I wrote it to match how our brains work, how we think. I appeal to our brains being pattern matching machines. I emphasize repetition. That is how we learn. Exceptions and breaking patterns are hindrances. It is antithetical that electrons themselves should act in a contrary manner, they don’t. Exceptions are shortcomings in our knowledge. I cannot and do not wish to write a complete course textbook. The greatest weakness of my book is the challenge to match the topics in a class. The current solution is for students to exert greater effort to find and master the relevant reactions from A Guide to Organic Chemistry Mechanisms. In many cases, the simplest method of doing so would be to simply begin at the beginning and just start learning the mechanisms in the order in A Guide to Organic Chemistry Mechanisms. When the more difficult mechanisms become introduced in your textbook or class, then begin to search for them with the table of contents, index, or write to me. When you find something, do all of the mechanisms on a page. They’re generally related. Doing one will make it easier to do them all.

Finally, if any professor happens to read this and is interested in customizing A Guide to Organic Chemistry Mechanisms to their class or applying for an NSF grant, contact me, and I’d be happy to cooperate in any way I can.

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