Organlc Stereochemlotry COMPress, P. 0. Box 102, Wentworth, NH 03282 J. Philip Bays,
Hardware: Apple II family Components: 1 Program disk and 1 backup disk Level and SubJect:College-level introductory organic chemistry Cost: $75.00
This instructional package is intended to cover the concepts of stereochemistry as they are applied to organic molecules. The programs are most suitable for students in a two-semester sequence in organic chemistry. However, since the package is modular, parts could be used by students in a onesemester survey class as well. The one diskette package is self-documenting and is not accompanied by any other written material. The prompting given after booting the disk is explicit and students did not experience any problems in determining how to proceed. Before the menu is displayed the user is given an option of two different type styles. This will accommodate the differences between monochrome and color displays. Audible responses to entered input are also optional. This feature is particularly refreshing for those who become annoyed or intimidated by hearing an obnoxious huzz after each incorrect response. The main menu contains eight tutorials and drills: (1) Stereochemical Definitions, (2) Assigning Absolute Configurations, (3) Fischer Projection Configurations, (4) 3-D to Fischer Problems, (5) Fischer Projection Problems, (6) Two Chiral Center Tutorial, (7) Two Chiral Center Problems, and (8) Cyelohexane Stereochemistry. The option to return to this main menu during any individual lesson is almost always available. Once a lesson is completed the menu selection is marked for user reference. Although any topic may he chosen, following through the menu sequentially is preferred. In many cases, a tutorial or problem drill will depend upon using the information presented in a previous topic area. For example, it would he difficult to attempt "Fischer projection' configurations" without first going through the tutorial on "assigning absolute configurations". When prior information is necessary, it is usually indicated on the first page of the tutorial.
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texts, and no obvious mistakes were found. The author uses several interesting analogies. A Fischer projection is compared to a bowtie with an interesting animated character to belabor the point. Assigning R & S configurations is elucidated by comparing the process to holding a flower by the stem (lowest priority group) and looking at the three petals. There are a few omissions that are generally included at a class of this level. Although plane polarized light was mentioned when discussing enantiomers, it was never explained and the concept of optical activity was conspicuous by its absence. The fact that the discussion of determining group prioritiesfor R & S configurations did not consider multiple bonds was also disturbing. Although molecules with two asymmetric centers are covered in some depth, including diastereomers and meso farms, compounds with more than two centers are not mentioned. The often used 2" rule was not considered. The most impressive module in this package is that dealing with cyclahexane stereochemistry. I t is the only main menu item that contains a submenu. Introductory material includes: equatorial and axial positions, conformational stability, structural isomers, and geometric isomers. The only major omission is the failure to discuss the process of intereonversion of conformations by ring reversal. Several types of comparison problems are presented. The user is asked to determine the relationship hetween pairs of randomly generated disubstituted cycloheaanes. The drill is enhanced by a "HELP" mode which allows the user to rotate one of the members of the pair about any axis or to undergo a conformational change for purpose of comparison. This aspect of the program is the best utilization of the computer that I have seen in practice1 drill software. It allows the student to manipulate the molecule without using models. This helm in visualizine two-dimensional representntiona as they are required t t , du in class and on cests. 'The manipulations do
During each lesson, the option either to review the most recently presented material or to continue is given frequently. This allows a student to repeat a small portion of a tutorial instead of repeating the entire lession. Most students found this very valuable. During a tutorial several examples of each concept are offered, although it is possible to continue after only one example if the user feels confident. In problem drills, the student is given the opportunity to drill for hours since the problems are randomly generated. This is a particularly good feature since there are many permutations and the same problem will hardly ever he repeated. One flaw with this type of problem generation is that branching to either easier or more difficult problems is not possible. Most problems within any particular drill seem to he of comparable difficulty. Surprisingly, most students did not find this a disadvantage, and the poorer students simply needed to drill many more examples before they felt comfortable with the material. Prompts are easy to understand and generally consistent. The options available at each input point are always indicated. Repeated attempts at meaningless inputs did not cause the program to crash. In fact, the computer would not even echounreasonable input characters. Usually a one Letter response is all that is required. The one exception is in the "3-D to Fischer Problems" drill. In this case when comparing two Fischer projections the user must indicate their relationship by answering either "IDENTICAL" or "ENANTIOMERIC". This is confusing since "I" or "E" is all that is required for the previous and subsequent drills. The program does differentiate between s response of "I" or "E" from other input by indicating that the error is "SPELLING". Perhaps the author felt that learning the proper spelling of these words was important, hut most of those who were not adept at typing simply found it annoying. The pedagogic development of the material parallels that given in most standard
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Summary Ratlngc: RevIeww I1 Owd
Category Ease of Use Subject Matter content
Excellent ExCsllem Excellent
PedsgDglc Value Student Reaction
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Computer Learning Package
Reviewer
J. Phillip Bays, Organic Stereochemisby
Rodney B. Finzel
Books
Forrest Frank
Monographs
New Volumes in Continuing Series
All8
Journal of Chemical Education
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require some practice to master, but the practice enhances the mental visualization process. Approximately 25% of the students in the class used this optional software package. AU found it to be useful in the conceptudizatiou of 3-D molecules. In fact, despite repeated attempts to elicit negative reactions, nothing but praise was obtained. Several tutorial programs are available for this course and this is the first package that obtained unanimous approval. The average student worked for P5 hours on the software with many spending considerably more time at drilling the randomly generated problems. I found this software package to be of great value. It iseasy touse and has obviously been thought out well by the author. It utilizes the comouter as more than a "video textbook", which is one of my major complaints against many other computer-assisted instructional packages. Many of my students found it to be invaluable in the learning of t h e 3-D visualization of 2-D ~roiections.It would be an ideal f i s t purehaie for those organic chemists who have not yet started using computer software as an instructional aid. Rodney 6. Flnzel Hotsba University
Hempstead. NY 11550
This is an excellent program about organic stereochemistry for two specialized groups of persons, t h m t a k i i sophomore college Organic Chemistry and others wishing a review. The subject of this program is organic stereochemistry, a difficult subject for many students and a trying one to many teachers wbomust emlainexamolesreoeatedly to students. ~ h patience ; of thecomputer is appreciated here by my students, for they can Lake as much time as necessary before answering each question and can do as many examples as they wish. I welcome thisprogram, which provides not only excellent instruction but also many drill problems. I keep the program on reserve in the media center for students to use whenever the" wish. ~-~~ The programdeals with the configuration around one and two chiral carbons and cycloheaane structures. It has eight pans, all run from one menu so it ia easy to change between the parts. Five are primarily tutorials, and three are primarily problems. A common format is used for most of the problems: two structures me drawn at the top of the screen and a series of questions is asked about their relationship. Wrong answers are responded to with the word wrong, which disappears in about 5 seconds, and then one is required to answer again. After each series of.answers, the student is given the choice of another example or going back to the main menu. My students like this because they can determine how long to spend on a topic. The fourth menu item deals with changing three-dimensional structures (drawn with wedge and dotted lines) into Fiseher projection drawings. Two drawings are given, one as a Fischer and the other as a 3-D drawine. Four choices are eiven. one a t a time: (i)Is there a chiralcerkr? (2) Are the twostructures identical or enantiomers? (3)
II Is the contiguratidn R or S? and (4) Do you wish another problem? The fifth menu item deals with two Fischer drawings and their relationships. The same questions as above are asked. The sixth and seventh menu items expand the study to Fischer drawings with two carbons. Questions are asked about the chirality of two of the centers followed by whether the two structures are superimposable and if so why. The stereochemistry of cyclohexane structures is the subject of the eighth section, which shows disubstituted cyclohexanes in dearly drawn chair conformations. This section instructs and drills on cis-trans isomers, stability of conformations, and naming of the cyclohexanes. It shows two cyclahenane structures and asks whether they are identical, conformers, geometric isomers, real enantiomers, or have different ring substitution. These problems include a feature which almost makes the disk worthwhile by itself. Help in deciding the relationship between the two cyclohexanes can he requested by pressing the H key. A set of five options appears a t the left side on the screen. These allow the user to rotate one of the rings around any of the three axes or change to the other conformation and see the changed structure as a third figure. This encourages students to d a y around with rotations until spatial relationships are understood. There is no external documentation with the disk, but this lack causes no problem for the user, because the prompts are excellent and wrong answers receive correcting responses. Overall, the program is very user friendly. No errors could be found in the program. I tried but couldnot erasb the disk with improper inputs. I think every schwl should have a t Least one copy available to students taking Organic Chemistry; they will appreciate it! Forrest Frank Illinois Wesleyan Universny Bloornlngton, IL 61701
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Press: New York. NY. 1985. xli 466 pp. Figs. and tables. 15.5 X 23.5 cm. $28.95.
Atmospheric Chemlrtry: Fundamentals and ExperlmentelTechniques Barbara J. Finlayson-Pitts and James N. Pins, Jr. Wiley: New Ycfk, NY, 1986. xxvlil 1098 pp. Figs. and tables. 16.5 X 24 cm. $59.95.
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This volume is designed to he a text or reference hook based on an integrated approach to the chemistry of anthropogenic and biogenic species present as gases, or in droplets and partides in both the natural and polluted troposphere.
Atomic, Molecular, a& Solld-State Thsory, Scatterlng Problems, Many Body Phenomena, and Computatlonel Quantum Chemistry Per-OlovLowdln(Editor). Wiley: New York, NY. 1986. 754 pp. Figs. and tables. 15 X 22.5 cm. $200.00. International Joumal of Quantum Chemistry. Quantum Chemistry Symposium No. 19, 1985.
Bask Tables tor Chemlcal Analysis ThomasJ. Brunoand Parls D. N. Svoronos. NBS Technical Publications: Washington. DC. 1986. v 233 pp. Figs. and tables. 21.5 X 28 cm. $11.00. NBS Technical Nde 1096.
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Tables of important data for use in the analytical chemistry laboratory are provided in this volume. These tables contain information for use in gas chromatography, liauid chromatoeraohv. " .. infrared and ultraviolet spectrophotometry, mass spectrometry, and wet chemical techniques. Tables relating to safe practice in the analytical laboratory are also included.
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Monographs Crystallographlo Computing 3: Data Collection, Structure Determlnatlon, PrOteIns, end Databases G. M. sheidrick, C. Kruger, and R. Goddard (Editors). Oxford University Press: New York, NY, 1985. Ix 314 pp. Figs. and tables. 16 X 24 cm. $35.00.
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lntroductlonto Chromatography, Second Edltlon Roy J. Griner, James M. Bobbin, and Arfhur E. Schwarting. Holden-Day: Oakland. CA. 1985. 289 pp. Figs. and tables. 15 X 23 cm. This bwk is designed to contain enough information so that a beginning student (or chromatographer) can obtain, in fairly short h e , an overall picture of chromatography.
Molecular B e a m Norman F. Ramsey. Oxfwd University
Ballerles lor Implantable Biomedical Devlcee Boom 6. Owens. Plenum: New York, NY, 1986. xix 358 pp. Figs. and tables. 15.5 X 23.5 cm. $55.00.
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Chromatographic Methods, Fourth Edltlon A. Braifhwaifeand F. J. Smith. Chapman 8 Hall: New York. NY. 1986. x 414 DO. Figs. and tables. 15.5 X 23 cm. $65:60 (HB)/$27.00 (PB).
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This book is the completely revised and updated version of the previous edition that was authored by R. Stock and C. B. Rice. It presents aunified introduction to the general theory of chromatography followed by a (Continued on page A118)
Volume 64
Number 4
Aprll 1987
A117
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Modern Techniques ol Surface Science
REVIEWf
D. P. Wocdruff and T. A. Delchar.
detailed treatment of the principles and practice of all the major techniques currently employed in researchand industry. There are separate chapters covering plane d m matography, including TLC, paper, electrophoresis, immunoelectrophoresis, and isoelectric focusing; gas chromatography; column c h r o m a t o g r a p h y ; a n d high performance liquid chromatography. Further chapters cover important new developments such as computerized data collection and microprocessing and the emergence of combined techniques. The final chapter contains a series of model experiments illustrating the use of the common techniques.
Electrophoresis: Theory, Technlquer, and Blochemlcal and Cllnlcal Appllcatlons, k m d Edklon A. T. Andrews. Oxford University Ress:
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New York, NY. 1986. xv 452 pp. Flgs. and tables. 16 X 24 cm. $49.95 (HB)I $29.95 (PB).
Handbook ol Coordlnatlm Catalysis In Organlc Chemletry Penny A. Chalomer. Buiterwow Publishers: London, 1986. 1002 pp. Flgs. and tables. 17 X 24 cm. $110.00.
Cam-
bridge Unlversiiy Press: New York. NY. 1986. x 453 pp. Figs. and tables. 14 X 22.5 cm. $89.50.
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This book describes the physical basis and anolications of all of the ~rincinletech&. niques, and most of the lesser techniques, used in surface science today.
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lnhoductlonto Organlc Photochemldry J. D. Coyie. Wiley: New York, NY. 1986. xiii 176 pp. Figs. and tables. 15 X 23.5 cm. $31.95.
T. E. Clanshaw, B. W. Dale, G. 0. Long worlh, and C. E. Johnson. Cambridge University Ress: New York, NY. 1986. 119 pp. Flgs. and tables. 15.5 X 23.5 cm. $29.95 (HB)1$12.95 (PB).
Orbitals, Terms and States Mslmlm Gerloch. Wiley: New York, NY, 1986. xii 176 pp. Figs. and tables. 15.5 X 23 cm. $31.95.
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Polymers In Solution: Theoretical Conslderatlonr and Newer Methods ol Characterlzatlon Wllllam C. Fwsman (Editor). Plenum: New 303 pp. Figs. and York, NY. 1986. vii tables. 15.5 X 23.5 cm. $52.00.
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Morton M. Denn. Wiley: New York, NY, 1986. xi 324 pp. Figs. and tables. 16 X 24 cm. $34.95.
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Thermodynamic and Transport Properties of Coal Llquldl Constantine Tsonopouios, John L. Heis man, and Shuen-Cheng Hwang. Wiley: New York, NY, 1986. xviii 214 pp. Figs. and tables. 16.5 X 24 cm. $49.95.
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The volume focuses both on equipment design calculations and on those coal liquid nrooerties needed in heat and material bal . . ances: vapor pressure, vapor liquid equilibrium, densities, and surface tensions. I t also evaluates recent research on EDS, SRC-11, and other direct coal liquefaction processes. Two alternative approaches for property prediction are discussed: one based on hoiling point and specific gravity, the other on critical constants and the acentric factor.
Journal of Chemical Education
Frederick A. White and George M. W d . Wiley: New York, NY. 1986. xx 773 pp. Figs. and tables. 17 X 24 cm. $72.50. This book provides an interdisciplinary treatment of modern mass spectrometry in its varied forms as well as its applications in a widevariety of fields. Part One begins with an introduction detailing the relevance of mass spectrometry in industrial research and development, its historical evolution, and earl" salient measurements. Various aspects o
