"Organic chemistry just now is enough to drive one mad."

Friedrich Wohler, in a letter to his mentor, J. J. Berzelius, 1835

 

"Tradition is no substitute for truth."

Andrew Radford, Transformational Syntax, 1988

The history of organic chemistry as a discrete science stretches back over nearly two centuries. Over these years, a few shreds of experimental data have grown into a mountain of information on the structures and reactions of organic molecules. The question of whether this body of information has made the science easier to comprehend or ever more maddening is a personal one, whose answer depends in large part on the teachers and literature from which one has learned.

Despite occasional cautions against getting mired in the land of "historical chemistry," I still revel in the papers of past decades, particularly those from the heyday of physical organic chemistry. Sadly, I'm too young to have attended the infamous UCLA colloquia in the days of Winstein and Cram, to have participated in a Woodward a group meeting, or to have taken part in the ferocious debates over the nature of the norbornyl cation. Nonetheless, I feel that an eye to the past is essential for moving strongly into the future, and wish that a bit more history made it into our teaching of chemistry.

Much wonderful information can be found at the Classic Chemistry website, compiled by Carmen Giunta of the Le Moyne College Department of Chemistry.

An interesting collection of essays on "Physical Organic Chemistry for the 21st Century" can be found in Pure Appl. Chem. 1997, 68(2).

An interesting collection of articles recounting the early history of ferrocene can be found at the beginning of J. Organomet. Chem. 2001, 637-639.

My interests in both research and teaching, coupled with an affinity for handling old books, have lead to a collection of chemistry books, mostly organic, that continues to grow out of hand. The collection spans two centuries of books whose authors' (ranging from researchers to artists) primary goals have been teaching science to graduate students, undergraduates, and the general public. I'd like to think that the diversity of books included provides some insight into the evolution of the science of organic chemistry as well as the development of the scientist-teachers that have populated it.

The collection won First Prize for Graduate Students in the 52nd Annual Robert B. and Blanche Campbell Student Book Collection Competition, sponsored by the UCLA Library in 2000, and has grown considerably since that time.

My favorite volumes include:

Comstock, J. L. Elements of Chemistry; In which the Recent Discoveries in the Science are Included and its Doctrines Familiarly Explained; Robinson, Pratt, & Co.: New York, 1835.

From the preface of this, the 17th edition: "It is hardly necessary for the author of the following volume to make any excuses for its publication, since, notwithstanding the multiplicity of books on the same subject, there seems to be none, which are exactly adapted to the object for which this is principally designed... Of all the sciences, this [chemistry] is the most complete, in respect to its language - the order of its arrangement, the succession of its subjects, and consequently in the facility with which it may be learned. But from these perfections, arises the absolute necessity of becoming well acquainted with its first principles, before the student can derive and retain any useful knowledge from its study... To the moralist, this subject [the doctrine of definite proportions] teaches, that nothing has been formed by the fortuitous concurrence of atoms, but that even the 'stocks and stones' bear the impress of creative agency and design."

And from the introduction to Part III, Organic Chemistry: "There is another wide difference between organic and inorganic chemistry. The latter presents us only with compounds formed in consequence of affinity, or the attraction of the heterogeneous particles of matter for each other. But organic substances are formed by the action of peculiar organs, each organ being endowed with the power of producing different results from similar elements... But although he [the chemist] can decompose the products of organic action, and find the proportions of their elements, he never has been able to recompose or imitate these compounds.

The Reason Why: General Science; Dick & Fitzgerald: New York, 1858.

This book of questions and answers is described on the the title page as a, "collection of many hundreds of reasons for things which, though generally believed, are imperfectly understood... a book of condensed scientific knowledge for the million." The top of each page bears a verse from the Bible, hinting at the relationship between science and religion at the time. At the outset, the importance of carbon for life is discussed: "Why is oxygen necessary to life? Because it combines with the carbon of the blood, and forms carbonic acid gas." In light of all that we have learned in the century and a half since this book was written, this statement may be regarded as one of the greatest oversimplifications in history!

Boston Journal of Chemistry and Popular Science Review, Volume XVII, Number 3; Journal of Chemistry Co.: Boston, 1883.

This tabloid-style journal is of particular interest to me since I grew up in and around Boston. Of note is an article, entitled "Naphthalene," which first summarizes the basic principles of organic chemistry and then proceeds to describe the history, chemical reactions, and applications of the hydrocarbon naphthlane. In addition to articles on chemistry, this volume contains many exquisitely illustrated advertisements for products such as "Horsford's Acid Phosphate," "Philips' Palatable Cod-Liver Oil," and "Colden's Liquid Beef Tonic."

Remsen, I. An Introduction to the Study of the Compounds of Carbon or Organic Chemistry; D. C. Heath & Co.: Boston, 1907.

Ira Remsen was President of the Johns Hopkins University. This is the 4th edition of a classic text (the first edition appeared in 1885). An interesting "Note for Student" reads, "Although the reactions above briefly described may at first sight appear to be difficult to comprehend, they are in reality simple enough. The student is earnestly recommended not to slight them on account of the long names and complex formulas involved." This remains excellent advice today!

Pauling, L. and Hayward, R. The Architecture of Molecules, W. H. Freeman & Co.: San Francisco, 1964.

This wonderful book consists of brief (each a page or less) essays by Pauling on various organic and inorganic chemical structures, each accompanied by an illustration by Hayward. At the time of its publication, images of molecules were rare - personal molecular model sets were not so common as they are today, nor were many of the physical tools and theoretical concepts that are now routinely used to elucidate and describe molecular structure.

Brown, H. C. with comments by Schleyer, P. v. R. The Nonclassical Ion Problem, Plenum Press: New York, 1977.

This book provides an account of one of the most ferocious debates in the history of organic chemistry. Although written by one of the two primary opponents in the debate, a balanced treatment is provided by "rebuttal" sections at the end of each chapter - this makes for a very unusual and very entertaining treatment of the subject!