Kinetics and Mechanisms; Molecular Modelling and

Chemical Education Today edited by

Book & Media Reviews

Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600

The Molecular World, a series The Third Dimension Metals and Chemical Change Kinetics and Mechanisms Molecular Modelling and Bonding Alkenes and Aromatics Separation, Purification, and Identification Elements of the p-Block Mechanism and Synthesis

coordinating editor L. E. Smart Royal Society of Chemistry: Cambridge, UK, 2002. reviewed by Paul Charlesworth

A quick search on Google reveals just how important distance education programs are for people who cannot easily attend bricks-and-mortar establishments. Opportunities for distance education are growing rapidly all over the United States, but probably the oldest and largest distance education program is that of the Open University (www.openuniversity.com, accessed Jan 2004) based in the United Kingdom. Royal Charter established the Open University in 1969. Since then it has provided educational opportunities for more than 2 million people, and is currently the United Kingdom’s largest single educational institution, with more than 200,000 people studying its courses each year. The Open University has changed a lot in the more than 20 years since I watched professors dressed in long-collared pink shirts, lecturing on BBC2 television programs, in the morning. Although the Open University still uses television for content delivery, the dry lectures of old have largely been replaced by lavish television programs supported by beautifully illustrated Web sites (www.open2.net, accessed Jan 2004) and textbooks with high-quality CD-ROM-based media. This review focuses on textbooks that are part of a series designed for the Open University S205 course “The Molecular World” and published in conjunction with the Royal Society of Chemistry. The Open University Web site describes this eight-month course as providing a broad foundation in chemistry by introducing the fundamental ideas, principles and techniques, and by demonstrating the central role of chemistry in science. This is considered to be a level-2 course and assumes some background in chemistry, biology, physics, and earth sciences. Students without a suitable science background are recommended to take the S103 course “Discovering Science,” which investigates topics such as “Water for life,” and “Our world and its atoms.” Eleven books accompany the S205 course, but this review covers only the middle eight.1 The accompanying CD-ROM(s) are designed for use only with Windows-based personal computers, the Open University required platform. Much of the accompanying

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media uses QuickTime and a few other standard media formats, but its central components are Windows only. Despite this setback, I was able to view most of the materials using Virtual PC on my Apple PowerBook and get a good impression of the program. Each unit has an identical main interface, which is installed on the PC, along with several helper applications. The main interface seems to include a cool digital tape player that the instructor uses to describe a concept or walk you though a new software package. Although the main interface runs from the hard drive, all supporting media are stored on CD-ROMs and so students must carry CDs around if they have laptops. A wide variety of helper applications is included, ranging from Apple QuickTime and Adobe Acrobat to specialized molecular viewers such as WebLab Viewer Lite and Orbital Viewer. Each CD-ROM topic or activity is cross-referenced in the textbook to provide a closely integrated unit with carefully allocated study schedules. For example, the model-building component of The Third Dimension explores how atoms pack together in the solid state. This is allocated an estimated study time of 45 minutes and involved watching a talking head, accompanying text, and couple of plastic models. Although this is not Oscar-winning material, it conveys the concept with reasonable clarity. In contrast to this, Activity 1 of the Kinetics and Reaction Mechanisms book involves a more hands-on approach to concepts such as drawing structures with ISIS Draw, and correctly using curly arrows. It is clear from their layout and textbook cross-references, that the CD-ROM content is an important part of the overall course. The Molecular World series is, however, a set of books described as demonstrating the central role of chemistry in the sciences, and how a molecular approach is of importance to biological and earth sciences. As a second level Open University series, it is probably equivalent to the second and third semesters of an American student’s college education. The books focus on “organic, inorganic, and physical aspects of chemistry as they relate to the natural world and to industry”. There is very little reference to the “entry level” topics found in most general chemistry textbooks. Because of this, it was not easy to decide how best to review the individual books. Should I compare them to first year texts, to upper level texts, or simply avoid comparing them at all? I elected to present an overview of each book and make some comparison to texts I am familiar with. For the most part, the Open University books are at a higher level than first year texts, but a lot of their content would be of great value to first year science majors, and to their instructors. I found it interesting that the Open University cites books by Atkins and Jones (1) and by Kotz and Treichel (2) as background reading when these are considered premier books in many American universities. In general I was very impressed with the quality of each book’s content and layout, and feel that some of them would be a great addition to the first year curriculum for students with a strong science background, perhaps an honors course.

Vol. 81 No. 3 March 2004

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Journal of Chemical Education

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Chemical Education Today

Book & Media Reviews The Molecular World, The Third Dimension

edited by Lesley Smart and Michael Gagan, with contributions by Corrie Imrie Royal Society of Chemistry: Cambridge, UK, 2002. 240 pp, ISBN 0854046607 (paperback). $44.95

The Third Dimension explores the arrangements of atoms in molecules and in different types of solids through a discussion of metallic, ionic, and molecular structures. It is the first book in the Molecular World series, but is the third book in the Open University S205 course of the same name. This created a little confusion initially because I wondered how “entry level students” would handle some of the material presented. I know that many of my first year students would be lost without some basic introduction. It would have been nice for the Open University to have included books one and two (both of which appear to be called “Introducing the Molecular World”) so that some idea of the real starting point could have been made. The Third Dimension appears to be an amalgamation of what American textbooks would include in the categories of ionic and covalent compounds, metals, and solid-state materials. It is quite a logical combination, which concludes with a wonderfully illustrated case study on Liquid Crystals. While the approach will be familiar to those from across “The Pond,” it is rather a radical change from the textbooks I normally work with where ionic and covalent compounds are separated by about twelve or more chapters from the metals and solid state materials. In a personal communication George Bodner commented that metals and metallic bonding should be treated at the same time as, if not before, a treatment of ionic and molecular compounds, which is what the Open University does. The book is divided into three sections covering crystals (Lesley Smart), molecular shapes (Michael Gagan), and a case study about liquid crystals (Corrie Imrie). As I noted above, part 1 of the book dives directly into the subject of metal structures by presenting the packing arrangements of several common metals such as gold and sodium. The imagery and clarity is quite impressive, with a liberal mix of colorful 2D and 3D line drawings and photographs of the WebLab ViewerLite image, available on the CD-ROM. For someone with good spatial visualization skills, the line drawings are detailed enough to appreciate the shapes, but the ability to rotate these in the software package provides a much clearer view of the arrangements. While multimedia are not a new thing, the level of integration between the text and CD-ROM is very strong, perhaps more so than many of the other books in this series. Part 2, like much of this series, takes a rather different approach to the representation of molecules by first introducing the carbon atom and then diving into Newman projections, isomerism, and topics normally relegated to a few pages in the organic chemistry chapter of a general chemistry book. From the authors’ perspective, students’ appreciation of organic molecular shape and isomerism is of greater 338


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importance than ability to predict the shapes of molecules they will likely never encounter, such as SF6 or XeF4. I really enjoyed the case study on liquid crystals and the suggestion that they may represent a fourth state of matter. Despite owning more LCD-based gadgets than anyone really should, I knew very little about their chemistry. The case study covers types of liquid crystals, liquid crystal phases, displays, and even how liquid crystal polymers, such as Kevlar fibers, are produced. This case study beautifully illustrates a very important class of materials that will be of great interest to science and engineering students considering careers in the electronics field. The Molecular World, Metals and Chemical Change

edited by David Johnson, with contributions by Kiki Warr and Ronald Dell Royal Society of Chemistry: Cambridge, UK, 2002. 272 pp, ISBN 0854046658 (paperback). $49.95

Metals and Chemical Change explores the structure and reaction of metals beyond those introduced in book 3. In particular, it covers industrial extraction and the activity series. These concepts are examined from a thermodynamic and redox perspective. The book appears to be an amalgamation of what American textbooks would include in aqueous solutions, thermochemistry, metallurgy, electrochemistry, and the chemistry of group I and II elements. The case study extends the electrochemistry discussion to a closer inspection of batteries and fuel cells, both topics of great interest to our current science and engineering students who may be developing these technologies for the automotive industry. This book begins by presenting the reactions of metals with many different compounds and with aqueous solutions of other metals. The section on mercury discusses its properties and even has a picture of someone sitting on a pool of mercury, with the caption “Floating human beings seem to barely penetrate the surface.” I am not sure whether this is a real photograph or a little Photoshop trickery. There is not much else to say about the majority of this book since it ploughs rigorously though thermodynamics, redox reactions, and lattice energy. What I did find interesting was the use of thermodynamics to explain why some metals oxidize easier than others. This is something I have not seen in many of the first year texts I have taught from and it makes perfect sense to take this integrated approach. In most of the first year textbooks, it is common to talk about cell potential, free energy, and equilibrium, but this is usually little more than a few extra calculations for the students to work on. Any discussion of the activity series was treated in the solutions chapter and not clearly linked to thermodynamics. Even though the book does not have the linear approach of most American textbooks, I applaud its attempts to provide an overall sense of how the principles of thermodynamics are controlling the reactivity of metals. Where I feel this book falls a little short from an American perspective is the sparse discussion of metal extraction.


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Having said that, this is a book about chemistry designed to serve students interested in learning chemistry and not a general chemistry book designed to serve a multitude of subjects. Therefore, it cannot be expected to provide more than a page or two on a particular ancillary topic. In Britain, this topic would probably be addressed by geology students, perhaps in a geochemistry or metallurgy and mining class. The case study, Batteries and Fuel Cells, is very similar to the batteries section of most American textbooks. The case study is supposed to target fuel cells, but that topic barely fills four pages. I was left without any greater understanding of this important topic than I had before and was quite disappointed. The Molecular World, Kinetics and Mechanisms

edited by Michael Mortimer and Peter Taylor, with contributions by Clive McKee, Richard Taylor, Craige Williams, and Michael Gagan Royal Society of Chemistry: Cambridge, UK, 2002. 262 pp, ISBN 0854046704 (paperback). $44.95

Chemical Kinetics and Mechanisms has, I am happy to say, a somewhat misleading title. It explores the role of reaction rates and chemical kinetics, which is achieved using a CD-ROM-based math program. The mechanisms discussed focus on organic substitution and elimination reactions. From the title, one may assume the book covers chemical kinetics and reaction mechanisms from a physical chemistry perspective as they are usually presented in chapter 12 of most general chemistry textbooks. (I would love to know why kinetics is almost always chapter 12!) While the physical chemistry approach is executed in exquisite detail throughout part 1 of the book, the whole of parts 2 and 3 are dedicated to the mechanisms of organic reactions, which was quite a surprise. Part 2, focuses primarily on the importance of recognizing and understanding the different organic reactions, but ends the chapter with a very nice description of substitution reactions. Part 3, in contrast, is dedicated entirely to elimination pathways and products. A key feature of the parts 2 and 3 is the introduction and use of curly arrows to represent the movement of electrons during a mechanism and the tight integration with CD-ROM-based “electron pushing” exercises. The book concludes with a wonderful discussion of shape-selective catalysis using zeolites. Despite being one of the most widespread chemical materials in use today, with over 3.6 million tonnes being produced each year, zeolites receive little more than a couple of sentences in most of the first year chemistry texts on my bookshelf. It is not clear whether this class of compounds is considered to be of little interest, or simply too advanced for general chemistry texts, but I think many authors should give serious consideration to a group of materials with such interesting properties. The case study begins with a thorough introduction to natural and synthetic zeolites, their structure-function relationships, and how they are classified. This is followed by a delightful www.JCE.DivCHED.org

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discussion about shape selectivity and how molecular size and shape affect diffusivity in different zeolites. The case study concludes with several industrial processes where the shape selectivity of zeolite catalysts has led to some very interesting products. When I was a graduate student at Keele University (UK), about one third of our department was interested in zeolites. Since I moved to the U.S. in 1993, this is probably my first encounter with them. Thanks to this book, I will certainly be introducing zeolites to my students in the future. The Molecular World, Molecular Modelling and Bonding

edited by Elaine Moore, with contributions by Guy Grant Royal Society of Chemistry: Cambridge, UK, 2002. 152 pp, ISBN 0854046755 (paperback). $32

Molecular Modelling and Bonding, the second shortest book in the series, explores why molecules adopt particular shapes and how those shapes can be predicted. The book and its accompanying CD-ROM present another topic that is inadequately handled by most general chemistry texts: a nonmathematical approach to molecular and quantum mechanics. Most books I have used present molecular orbitals of a few select molecules, but never elaborate on their meaning, which leaves even my best students with that morning-after feeling. Molecular and quantum mechanics is a difficult concept for most neophyte chemistry students to master and our current slew of general chemistry texts do not help, but for under $40, I may just recommend this book in my second semester science majors course. The ability of modern software to rapidly convert numerical data into understandable three-dimensional representations cannot be ignored. Molecular modeling and simulation is clearly becoming a valuable research tool, which must be included at the undergraduate level. This book very nicely leads students though the basic concepts of quantum chemistry and molecular orbitals, by replacing equations with colorful images and line drawings. The book presents a single page on the basics of how modeling is performed and then refers students entirely to the accompanying CD-ROM where they work through a series of activities. The CD-ROM content in this section is a little dry, consisting of a combination of text, audio, and simulations, but it does convey the concepts quite adequately. However, I really would like to have seen more than two pages of information on this subject. Working from a CD-ROM is OK, and I recognize this is probably a course requirement, but there is something nice about the tactile nature of books. Furthermore, the lack of any textbook content would complicate classroom discussion where reference to material may be needed. Even though the case study, Molecular Modelling in Rational Drug Design, is only 20 pages long, it provides the reader with a useful insight into the computational methods used in drug design. It is very well illustrated with line drawings, equations, and photographs of the computer generated molecular interactions and structural relationships.


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Book & Media Reviews The Molecular World, Alkenes and Aromatics

edited by Peter Taylor and Michael Gagan, with contributions by Alan Heaton Royal Society of Chemistry: Cambridge, UK, 2002. 184 pp, ISBN 0854046801 (paperback). $34.95

Alkenes and Aromatics presents 184 pages dedicated to organic functional groups. It extends the exploration of organic reaction mechanisms introduced in book 5 with a discussion of addition reactions. This is followed by a detailed look at aromatic substitution and organic synthesis. The book actually seems more like an introduction to synthetic organic chemistry and is clearly a step beyond what we normally teach in the first year chemistry program. It contains material that would appear well into an organic chemistry sequence. The book is divided into four uneven sections covering addition reactions in alkenes, aromatic compounds, a first look at synthesis, and a case study on Industrial Organic Chemistry. Each equation in the book is supported by images on the CD-ROM. These images are three-dimensional representations of molecules contained within the equation. This is quite useful for students who need this kind of visual feedback. Other than these equations, the CD-ROM contains a set of questions and information about the software available. Both sections on alkenes and aromatics can best be described as an electron-pushers dream that covers all of the common reactions for these classes of compounds. The pages are filled with beautifully drawn elimination and addition mechanisms augmented with little red arrows depicting the movements of electrons. A first look at synthesis focuses on the preparation of drugs such as pseudoephedrine by guiding students through the design and synthesis of compounds with a particular structure-activity relationship. The synthetic steps are very interesting for someone with an appreciation of chemistry, but it probably involves a level of experience most first year students in U.S. universities do not yet have. The case study, however, is ideally suited to first-year students who are most likely to be engineers or scientists in a discipline other than chemistry. It provides a very nice overview of the types of chemicals and chemical processes that are important in industry. What I found particularly useful were the figures showing how many household substances are made from a particular precursor molecule and the types of reactions required to make each substance. For example, 11 different classes of compound are prepared from ethane. For many students, the ability to relate real-world compounds with the chemicals we present to them in class could prove very useful. The Molecular World, Separation, Purification, and Identification

edited by Lesley Smart, with contributions by Adrian Dobbs, Eleanor Crabb, Andy Platt, and Anya Hunt Royal Society of Chemistry: Cambridge, UK, 2002. 120 pp, ISBN 0854046850 (paperback). $29.95

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Separation, Purification, and Identification explores methods for separating and purifying chemical compounds. This is followed by an introduction to spectroscopic techniques used in the identification and structural determination of compounds. It is the thinnest book in the series and a logical follow-up to a book on organic synthesis. Clearly, once you know how to design a synthesis and make the compound, you will need to know how to purify it. The book is well written and illustrated. The accompanying CD-ROMbased spectroscopy content is the strongest of the whole series and is a good indication of what can be achieved with computer-based learning. I really appreciated the level of interactivity without the use of unduly flashy materials. Some of the suggested experiments are probably beyond most first-year laboratory students because they involve techniques such as nitrogen atmospheres and Grignard reagents. Furthermore, some of the reactions described require 8–10 hour refluxes in an oil bath. I clearly remember these reactions in my undergraduate classes, but at the general chemistry level we typically fit reactions in two 3-hour slots or carefully spread them over two weeks. Even so, the book is well worth reading, if not just for the CD-ROM-based spectroscopy tutorials. The Molecular World, Elements of the p-Block

edited by Charlie Harding, Rob Janes, and David Johnson, with contributions by Andrew Galwey Royal Society of Chemistry: Cambridge, UK, 2002. 305 pp, ISBN 0854046909 (paperback). $54.95

Elements of the p-Block, the second largest book in the series, is quite an encyclopedia of elemental information and imagery. It explores the chemistry of the p-block elements, their periodic trends, and uses in agriculture, industry, or everyday life. Other than a few general comments, the bulk of the book simply provides a thorough introduction to elements of the p-block. However, the authors see fit to include not only the elements but also sections on redox reactions, acids and bases, and chemical bonding along with sections on the industrial use of each element group. This provides students with some sense of how the topics are tied together. I must confess that in our first year program this is one of my least favorite topics to teach and I often relegate it to required reading, supplemented by problem sets. The reason for this is that most texts are rather dull when addressing these topics, and the chapters contain little material to challenge students beyond memorization. While this book is not a shining star, its questioning style is a little more refreshing and thought provoking. Between paragraphs there are short thought-provoking questions that encourage you to think about, for example, why an observed change is significant, and what you may attribute the observed changes to. The case study, Acid Rain: Sulfur and Power Generation, very nicely addresses the chemistry and impact of the different sources of sulfur in the atmosphere. Since a lot of British power stations are coal fired, a short discussion of coal and the sul-


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fur in coal is provided together with the chemical changes occurring in the atmosphere, soils, and lakes as a result of acid rain and how cleaning processes work to reduce emissions. The Molecular World, Mechanism and Synthesis

edited by Peter Taylor Royal Society of Chemistry: Cambridge, UK, 2002. 370 pp, ISBN 085404695X (paperback). $49.95

Mechanism and Synthesis explores strategies for synthesizing organic compounds, particularly those of interest to the pharmaceutical industries. The book explains how to plan reactions that lead to a particular product. It is by far the largest and most advanced book in the series. This near 370page monster is very clearly an upper level chemistry text. I remember some of the content from my undergraduate days at Keele University, but most of this I have not seen for a very long time. The book is divided into six sections covering carbonyls, organometallics, radical reactions, strategy and methodology, synthesis and biosynthesis, and a case study on polymer chemistry. While there is nothing particularly unusual about the sections in this book, the one that caught my eye was the discussion about strategies and methodologies. Although my undergraduate retro synthesis classes are part of my educational history, many of the topics presented in this section jog the old brain cells a little. The section walks students through the planning of a standard synthesis by describing how to select a precursor by performing different bond disconnections in the target molecule an working backwards. Each example is supported by a database of images on the CD-ROM, but the retro synthetic analysis tutorial was by far the most valuable component on this CD-ROM. By working through the interactive software I was able to identify the types of bond disconnections and functional group interchanges required to retro synthetically build the molecules. A nice feature of this was that once the retro synthetic step had been identified, I was guided through identifying an appropriate forward reaction. With the CD-ROM’s assistance a lot of retro synthetic mysteries can be solved. Considering the depth of information contained in this series, the case study, Polymer Chemistry, was very disappointing. I found it lacking in many aspects of polymer synthesis and properties.

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Concluding Remarks, The Molecular World Series Overall, this is a superb set of books for teaching chemistry at several different levels in a U.S. institution. Although it takes an obviously British approach to the organization of material, one that I remember somewhat from my undergraduate education, the approach and terminology could be readily adapted. I really liked the content and organization, but it is not for everyone. I do wonder how a lot of my first year chemistry students, who have very poor science backgrounds, would cope without several weeks of introduction to the basics of chemistry and independent study such as the Open University S103 course “Discovering Science.” For many instructors, simply selecting a few books to emphasize a particular content area would be very useful. Individual books are inexpensive and provide a lot of useful information. Of particular interest in this category would be books six and eight that cover molecular modeling and separations, respectively. For instructors who would like their students to consider chemical kinetics and mechanisms from a slightly different perspective, book five provides a wonderful introduction to mechanisms in organic reactions. Note 1. Books 1 and 2 “Introducing the Molecular World” and book 11 “Skills Development” are not included. According to the Open University Web site, Books 1 and 2 provide a survey of the role and scope of chemistry and some additional science background, while book 11 covers the use of chemical literature and databases, the writing of scientific articles, and the preparation and delivery of short talks.

Literature Cited 1. Atkins, P. W.; Jones, L. Chemical Principles: The Quest for Insight, 2nd ed.; Freeman: New York, 2001. 2. Kotz, J. C.; Treichel, P. M. Chemistry and Chemical Reactivity, 5th ed.; Brooks/Cole, 2003.

Paul Charlesworth is in the Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931; [email protected]


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Kinetics and Mechanisms; Molecular Modelling and

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