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October 10, 2005
Volume 83, Number 41
pp. 48–51


A Tale Of Two Textbooks

History and influence of Sienko & Plane and Morrison & Boyd detailed at symposium

Stu Borman

Millions of college students have learned general chemistry from “Chemistry: Principles and Properties” by Michell J. Sienko and Robert A. Plane and organic chemistry from the textbook by that name by Robert T. Morrison and Robert N. Boyd. But how many scientists know the stories of these books and their authors?

Courtesy Of Roger Egolf

Six And Counting Morrison & Boyd has gone through six editions, with a seventh in the works.

Theirs were among the tales told at a Division of the History of Chemistry symposium on “Landmark Chemistry Books of the 20th Century” at the recent American Chemical Society national meeting in Washington, D.C.

Sienko & Plane was the first modern chemistry text, said James L. Ealy Jr., assistant professor of education at Cedar Crest College, Allentown, Pa., and many modern general chemistry texts still follow its basic format.

The text's “straightforward and practical approach to first-year chemistry caused more than a few students to reconsider chemistry as a major,” Ealy noted, but “for many of us, this text opened the door to our future.”

Sienko died of cancer at age 60 in 1983, but Ealy has interviewed Plane, 78, who lives in Albuquerque, N.M.

In the mid-1950s, Sienko and Plane were young chemistry professors at Cornell University when they became dissatisfied with the textbook they were expected to use and decided to write their own. Their writing of the book was based on a series of rules that “were set in stone and were derived from what they did not like about the present-day freshman text,” Ealy said. The rules were as follows:

  • Write nothing that is not completely correct.
  • Do not oversimplify; instead, omit.
  • Do not write anything that doesn't help students understand the material.
  • Include nothing that is not given in our lectures; keep it short.
  • Every word will be agreed upon by both of us.
  • Do not look at any other textbooks; obtain information from primary sources.
  • Include lots of problems.
  • Distinguish clearly fact from theory.
  • Follow an outline of theory before descriptive chemistry to help students learn the most useful things.

Writing the book was a family affair. Sienko and Plane recorded their chemistry lectures on a wire recorder, an audio recorder from the days before the development of magnetic tape. Sienko's wife, Carol, transcribed the recorded lectures. Sienko and Plane each rewrote the other's lectures. And Plane's wife, Georgia, composed figures based on blackboard drawings from the lectures.

Sienko and Plane “used a ‘nodometer' system to see if they should change things in their lectures” and their book, Ealy said. If students fell asleep in class, they interpreted that to mean that a lecture was unclear or the material was too esoteric.

The two professors self-published the first edition of their book in 1957. “They wanted to publish 2,000 copies,” Ealy said. “Each was going to cost $3.00 to print and disseminate, and they were going to charge $4.00.” But they didn't have the $6,000 needed for the initial print run, so Plane borrowed the money from a local bank.

Courtesy Of Cornell University Courtesy Of Robert & Mary Plane



After the book was published, “word spread quickly among professors at other colleges that this was a book they could use,” Ealy said. “It matched their lectures, and the students liked it.” The thorough and often challenging problem sets at the end of each chapter were especially highly valued.

The book caught fire, metaphorically speaking, and four subsequent editions were published at approximately five-year intervals by McGraw-Hill. In 1974, Plane became president of Clarkson University, Potsdam, N.Y., and he and Sienko stopped writing new editions at that point.

In its heyday, the book enjoyed a level of dominance that would probably be difficult to achieve in today's more competitive textbook market, and “this wonderful textbook became a model for future textbooks,” Ealy said.

“Organic Chemistry” by Morrison and Boyd, associate professors of chemistry at New York University, became similarly influential in organic chemistry. The 1959 publication of the first edition of this textbook changed the pedagogy of the field “and influenced the education of a new generation of chemists,” associate professor of chemistry Roger A. Egolf of Pennsylvania State University, Fogelsville, said at the symposium.

Egolf said that when he first studied organic chemistry in college using Morrison & Boyd, he “found the material fascinating and the explanations in the book crystal clear. I even enjoyed working the problems in the back of the chapters. I decided that summer that I wanted to be an organic chemist. I continued to use Morrison & Boyd as a reference when I began graduate school and literally wore off the book cover.”

It has always been challenging to write an organic chemistry textbook that makes the subject easily understandable, Egolf said. “Edward Hart, author of a 19th-century organic chemistry text, wrote in his recollections, ‘For most of the textbooks on the subject that have been written, I have nothing but contempt. ... Most of them shoot far over the head of the average student, leaving behind stupefactions and discouragement.' ”

Most textbooks “simply went through the chemistry of the various functional groups, detailing the reactions used to make the various types of organic compounds and describing the properties of these substances. Textbooks written shortly before the introduction of Morrison & Boyd were still following this format.” Little if any information was presented on the mechanisms of organic reactions.

However, “by 1959 it was becoming clear that mechanistic explanations were the future of both the process and teaching of organic chemistry,” Egolf explained. “The time was right for the introduction of a thoroughly modern organic text.” Indeed, that year saw the introduction of two important new organic textbooks based on novel philosophies on how to organize the material: “Organic Chemistry” by Morrison and Boyd and a textbook of the same name by chemistry professors Donald J. Cram of the University of California, Los Angeles, and George Hammond of California Institute of Technology.

Cram & Hammond abandoned the traditional functional group approach. “It was a thoroughly modern book, different from anything written in the past,” Egolf said. “Its organization was very logical, covering structure, nomenclature, and occurrence of the main classes of compounds first, followed by chapters that included modern treatments of chemical bonding, stereochemistry, and the correlation of structure with properties and chemical reactivity. Only after those topics were covered were reaction mechanisms introduced.” The book also addressed advanced topics like rearrangements, heterocyclic compounds, polymers, and spectroscopy.

“The problem with Cram & Hammond was that it was too densely packed with material, which just kept coming at the students at a rate that could seem completely intimidating to a bewildered sophomore,” Egolf said.

At the same time Cram and Hammond were working on their book, Morrison and Boyd “were actively integrating modern structural theory and mechanistic explanations of reactions into their teaching of undergraduate organic chemistry,” Egolf said. “They observed that their students actually did better on traditional synthetic and analytical problems when trained in this fashion, as opposed to the older traditional memorization approach. Eventually, they decided to attempt to write a textbook that incorporated their teaching styles.” The publishing company Allyn & Bacon “agreed to take a chance publishing a book that was very different from what was currently available.”

Morrison and Boyd wrote in an easy-to-read style that was accessible to the average organic student. They did not totally reject the traditional organization of organic texts based on functional groups, as Cram and Hammond had done. Instead, they introduced theoretical and mechanistic explanations into an organizational framework based on functional groups.

A strong point was the book's excellent problem sets, Egolf said. Each set started with easy problems that built the confidence of students and continued with thought-provoking problems based on real-life research data.

The popularity of Morrison & Boyd grew, and the book soon began to influence the way other authors wrote their organic textbooks. “The old classical tradition of memorization without theoretical principles quickly died,” Egolf said. “Cram & Hammond had its devotees, but most professors found Morrison & Boyd more popular with students and easier to teach from.”

Some professors criticized the book's integration of mechanisms with reactions because they believed many mechanisms were speculative and subject to revision. Indeed, a few “opted not to use Morrison & Boyd because they thought some of the mechanisms were wrong,” Egolf said. But many others did not see this as a serious problem and adopted the book for their courses.

Courtesy Of Joan & Robert Morrison Courtesy of Roz Boyd



In 1964, another groundbreaking organic text appeared, written by professor of organic chemistry John D. Roberts and senior research fellow Marjorie C. Caserio of Caltech. “It took a much more chemical-physical view of organic chemistry, stressing thermodynamics and quantum mechanics and giving a thorough, modern treatment of NMR [nuclear magnetic resonance spectroscopy] two years before the second edition of Morrison & Boyd added that topic,” Egolf said. “The book has also had a great influence.”

Roberts tells C&EN that he credits “Organic Chemistry” by Caltech professor of organic chemistry Howard J. Lucas as the first to incorporate physical organic chemistry as a major theme. Roberts notes that the 1935 work was way before its time in doing so (J. Phys. Org. Chem. 2005, 18, 566).

Morrison tells C&EN that when he was a graduate student getting ready for his preliminary exams, he remembers going through Lucas. “I loved it-it was great,” he says. “And there's no question that Lucas' use of problems was a model for us” in the writing of Morrison & Boyd. “Lucas was 20 years ahead of his time, but his book just never caught on.”

At the symposium, Egolf pointed out that many other organic textbooks released in the years since Morrison & Boyd arrived have tried to copy its style and structure, with small variations in focus. “Almost all of them have incorporated the pedagogy of introducing mechanisms at the same time as the reactions to which they refer,” he said.

Certainly, the book has stood the test of time. The sixth edition of Morrison & Boyd, now 13 years old, is still in print and “is presumably still used by thousands of students per year,” Egolf said.

A symposium attendee noted that he began his academic career in 1959, “and the first time I taught organic I used the first edition of Morrison & Boyd. By the time I retired in the late '90s, I had taught from all six editions.”

Morrison, 87, says that he is currently working on a seventh edition of “Organic Chemistry.” But he is preparing the work without his longtime partner; Boyd died in 2000 at age 85.

Whether another edition ever sees the light of day, “the spirit of Morrison & Boyd will remain in organic textbooks of other authors for the foreseeable future,” Egolf said.



Other Classic Chemistry Books Recalled

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