Introduction to O r g a n i c Chemistry Stanlev Smith. COMPress. P.O. Box 102. ~ e n t v i o r t h ,NH 03282, 1981 $GOIdiskette, set of 7 for $350, extra (backup) diskettes $10 each Hardware: 48K Apple ll+e or Apple Ii" (or Apple Ilea according to publisher) Software: DOS 3.2, 3.21, or 3 3: Applesoft Components Alkanes and Alkenes; Substitution Reactions: IR and NMR Spectroscopy: Arenes: Alcohols, Aldehydes and Ketones: Carboxylic Acids Level and Subject: Sophomore organic Review I
I am a teacher who has not felt totally committed to the use of computer-based materials in the teaching of chemistry. However, in reviewing Stanley Smith's seven disks an "Organic Chemistry," I became aware of the compelling power of the medium. This program may represent the best in computer software a t the present time. Stanley Smith is an old master of a very new art and there are many instances of his mastery here. Nonetheless, in reviewing such a program one must judge its comparative merits with respect to other lung-established methods of teaching: the classroom, the l a b oratory, and the textbook. One must evaluate what the computer, with ils instant response, vivid eraohies.. and infinite oatience. can do supremely well as apposed to what a competent instructor can provide in flexibility and responsiveness. The author intends the seven modules of the program to constitute "a short course in organic chemistry suitable for individual home study or t o be used as asupplement t o a colleze level course in oreanie chemistrv." i> he p n :r:\>u i. ~ ~ m ,Ie chg ~ i, ~ v ~ r . . ~,,I,!>s !~,".,r~..i,v , , W % + . r,,,.,,\ .t,!..cry 1. I ~ C . O ~
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~ o s e d .I t could also serve for a student needing a refresher course in organic chemistry. Although the package includes a substantial fraction of the topics included in traditional two-semester organic courses, i t does not approach them (nor even many one-semester courses) in comprehensiveness. Furthermore, it cannot stand alone. Not only is its content incomplete, but also the average student, coming to i t for the first time without any background, often would be lost. The expository material given on the disks is incomplete and some introduction to most of the topics uia lecture or textbook is probably necessary and certainly highly desirable. The disk's main weakness lies in the thin coverage of some topics and in the complete omission of others: alkynes, stereochemistry (RIS), amines, ethers, phenols, esters, amides, carbohydrates and proteins. The IRINMR module, one of the best in the series, takes advantage of the Apple 11's reasonably good resolution graphics to depict IR and NMR
spectra. The graphics may suffer a little in comparison with high resolution spectra, but to have them in context is of great benefit to the student, especially where there may be no IR and NMR spectrometers available. This
Summary R a t i n g s Reviewer I Ease o f Use: Good-Excellent Subject Matter Content: Average Pedagogic Value: Ranges from below average t o excellent depending on unit Student Reaction: Good Reviewer II Ease o f Use: Excellent Subject Matter Content: Good Pedagogic Value: Excellent Student Reaction: Good
mis issue of the JOURNALcontains the first two in a series of computer-based instructional material reviews that are sponsored by NSF Development in Science Education through Project SERAPHIM. Both reviews are careful examinations of Stanley Smith's Fdisk "Organic Chemistry." published by COMPress. Inc.. for ~- the- Annle 11". m e m crucon,pner r e . ~ o l na r~c.cea ~ ~ h rori e m a incrc.tsea the s mp c i u~f LS ng computer-oa5w rnxere 5 SL inid of ., comp.wr. w a l e or nut O ~ . Cme oppon..n.n tu nccrporae compi.wr exerc sas WOOJI 'each ng rncrl.~,t an s rno..o r e ? Tuansner m a t q m s on rerla\ens*el:re. cucrrilnatner students to use the programs for several months and to report the strong and weak points of boththe programs and the computer medium itself. We have not restricted our selection of reviewers to chemists with prior experience using computers. (Anyone who has a microcomputer, is interested in reviewing programs, and has not yet completed a Projed SERAPHIM Interest Form should write to me to volunteer.) We have asked reviewers to make critical comparisons among CAI, books, lectures, laboratories, and other modes of instruction. Since CAI is in its infancy, this may onen result in lessthan completely ecstatic reviews. Nevertheless. as the reviews in this issue demonstrate, there are already many areas (and many specific compuier lessons) in which the computer is by far the winner in competition with ciassical methods. We believe that honest, critical reactions from chemists who are neither pro- nor anti-computer will convince many who have so far dismissed CAI arbitrarily that they have been missing something. Instructional computing has advancedtothe point where the average teacher. notthe computer nut, is using CAI and purchasingcomwill provide a useful guide for any teacher mercially available programs. We hope that reviews in T H ~ SJOURNAL who has to choose whether to buy and which programs to select. Jahn W. Moore
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Reviewed in this Issue 7 Computer Learning Package Review Reviewer
Stanley Smith, lntroduction to
T a m a r Y. Susskind Alan H u t c h c r o f t
Organic Chemistry
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Books C. W. Keenan, D. C. Kleinfelter, and J. H Wood, General C o l l e g e Chemistry,
Sixth
Jeffrey A.
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Hurlbut
Edition
A184 A184 A185
Continuing S e r i e s Titles o f
Interest
Symposia
V o l u m e 60
Number 6
June
1983
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module is one of the few that can stand alone, and the author manages to incorporate IRI NMR spectra in later modules very effectively. The student should understand the material covered in this disk before attempting the modules on alcohols, aldehydeslketanes, and acids. There are no major technical difficulties in running the program, and its use requires little or no experience. If you know how to insert the disk and turn on the Apple 11,you are on your way. The instructions are sparse hut sufficient, and the prompts, with few exceptions, unambiguous. The index seems hare-boned; the titles in the main index and suh-indices could he more informative. Perhaus a comolete index (outside of the com-
help hefore answering the question. The computer gives hints and clues and aslong as the correct answer is typed in, the student aets full credit. Somethina is inconsistent here. The oarts of the oroeram that deal with is not limited to it. The points which need to be more fully addressed deal with commas, hyphens, and the separating or stringing tagether of words. In the alkanelalkene module there is no mention of the rules of ~ u n c t u a -
pinpoint the mistakes, e.g., hyphens or commas omitted, but respond, for the most part, with the correct answer. There are ineansistencies which need to he worked aver, far instance: t-butyl is acceptable but tert-butyl is not; i-propyl and isopropyl are fine but not isa-prapyl. In the arenes disk more care could be taken with how and when words are separated: vinylbenzene is acceptable for styrene but phenylethene is not. There are no substitute names for anisole and acetophenone. In the alcohols disk too much time is spent on the rarelv used carbinol nomenclature: it mieht wefl he deleted. In the aldehvdeketone
guew, for instance, that Newman projections are found in the introduction to alkanes? In working through the programs the imposed regimentation of the medium is soon apparent. The computer tends to take an a relentless personality and the options are few: to type answers, right or wrong, to go back, ta get help, or to escape to the lesson index. Thii forced discipline is attractive for mine but positions are bypassed in aldehyde and acid stifling for others. The student should he able nomenclature because the keyboard has no t o advance, by-passing questions which may way of handling them In the ketone nahe too simple or that have been answered menclature, acetophenone can be called before. There should be the freedom t'o temmethyl phenyl ketone but not phenyl methyl ketone: acetone can he called dlmethvl ketone oorarilv Dass aver.a auestion that seems too , ~ d ~ t i ~ c u l r , olnwn 1h.11i. in I:LI. ~ v . ~ ~ lin~ l d e rhc quwwror ihr IUII m t rlulcs. \n.,thrr characteristic of this program (and perhaps adequacies, combined with the ineonsistenall programs), is that the student cannot go cies, are bound to annoy a good student and hack to any spot withinalesson, as in a textconfuse a had one. hook. One has to work through the index and Drawing structural formulas is straightthe sub-index, and then often respond to forward except that the computer program questions answered previously in the doesn't permit commencing with anything lesson. hut amethylgroup or halogen. For instance, Same input responses could he simplified so that the student is less likely to be stopped one cannot construct l-chloro-2-methyl pro^ short by spelling errors. The author allows pane hy using the seemingly legitimate order of CH2, C1, C, CH3, H, CH3. A somewhat "Y" and " N for yes and no and sometimes perverse attempt to construct 3.3-dichloro"P", "S", "T" for primary, secondary, or pentane by starting with a C1 followed by a C, tertiary. Why, then, are single letters not accepted for the following responses: "I", "D" a second Cl and then a CHz broke down with for increase, decrease; "0". "R"; for axidathe stern but unhelpful rebuff "use a methyl tion, reduction; "A", "T" for absorption, or halogen here." Clearly the computer is transmission; "S", "D" far same, different getting rattled by these antics. In the rest of the material i t is possible to baek-space and ete.? Although the printed message responses erase errors one letter a t a time. In writing are always there, the audible output restructures, however, errors may he corrected sponses are inconsistent. Sometimes the blips only by erasing the entire entry and starting are immediate, sometimes the return key has to be hit, and there are times when there is no over. This can be frustrating and time canaudible resoanse a t all. At all times the stusuming. At times i t is unclear how much previous knowledge the author presumes. Questions wrong, the computer usually coaches the are asked with no introductory foundation: student with the correct answer and there is "Do you think methane is flat the way it looks in the drawing?" or "Is hydrogenation of cyclohexene to cyclcohexane exothermic or endothermic?" In the latter context the au" .. outer militates aeainst anv error whatsoever thor states that catalytic hydrogenation gives "cis" addition whereas bromine adds "trans" in i e x i drills, p r ~ s U ~ I I A , ~ n qubm.. d 'l'hs . < I W W ~ Im dy r t m r ~ I 3,) tni~t.al+ r m r ! V I I ~ C . U I to the double bond. These days, most organic heing prompted, but the computer does not textbooks distinguish between mechanistic recognize the corrected response in grading and structural descriptions. The "cis-trans" combination is reserved for the structural the quiz. The question goes into the hank and description; the "syn-anti" combination is is repeated until the student eels it right an used to describe the mechanism. Another the first try. On the other h k d , in certain term that has undergone a metamorphosis of quizzes, the student has the option of seeking
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Journal of Chemical Education
sorts is the "carbonium ion"; modern texts refer to the species as the "carbocation." Undefined terms are sometimes used, e.g., isomers, concerted, chirality, shielding. The program is not totally free of spelling errors and typos. For instance, the author writes, "Tertiary alkyl halides are not effected [sic] by . The author asks "What is it's IUPAC name?", and the possessive "its" has an apostrophe elsewhere as well. Admittedly most of these will blow right by the average student. In the alcohols unit. rather than ask
. . ."
eration is undergoing oxidation or reduction. In the same unit there are a few clumsy statements, e.g., "Name the longest chain alkane which contains the OH group" rather than "What is the name of the alkane that questions can he reworded to accommodate a yeslno response, thereby removing any doubt about the expected response. An enample of a question is: "Is HOH s better or poorer leaving group than OH?" The same thine can be accomolished bv askine whether possible responses and in these programs it does not. When it can we've got to start wondering what our role is. Far the question "What happens to the rate of racemization if you double the concentration of LiBr?" it rejects "doubled" and "it is doubled" hut accepts "double," "doubles," "it doubles," "it double." The subject matter material and practice problem sets vary considerably in difficulty: from too simple to quite challenging. The treatment of the material also varies from detailed descriptions in some sections to a mere glossing in others. The subtleties described in the nitration mechanism go far beyond what one might expect, yet the explanation is abrupt. The one example each for the oxidation ofthe alkyl group in arenes and the carbonation of Grignards is surely insufficient. Many reactions and mechanisms, e.g., hydrogen-deuterium exchange, oxime formation. acetal-ketal formation, are described in great detail, but the treatment of nomenclature is everywhere inadequate and subjects of comparable importance are totally omitted. The practice problems in the alcohol and arene sections are a t the right level: well-balanced, challenging without being baffling, and with adequate help resoonses. Those on the aldehvdeslketones and
not extensive enough; there are more repeats than one would like. In the IRINMR disk more could be said about the IR absorption bands of esters and how they compare-with aldehydeslketones. It has some awkardly worded questions, e.g., "Is it just as likely that 3 spins are up as it is that 2 are up and 1down?" There must he a better way of asking how the spins are distrihuted. NMR "lines" might better be referred to as "peaks." There are some in con^ sistencies in the inputloutput responses for NMR. The computer gives the chemical shift of the methyl group on the end of an alkyl (Continued on page A1821
VIEWS chain to be between $ = 0.9-1.5, hut allows only 0.7-0.9. Similar inconsistencies can he found with the inputloutput responses for the chemical shift of amethyl next to a earbonyl, the vinyl proton and the proton on a benzene ring. The most imaginative disk in the series is the one on "Mechanisms of Substitution Reactions."Like the IR/NMR disk it has the ability to stand alone. The color animation capability of the Apple is graphically demonstrated, and it is here thst the computer is clearly superior t o the instruetorltextbook combination and represents an advance in the teaching of reaction mechanisms. It is uarticularlv rewardine to view on the screen 11,- me 1,s old .>thvr. xr iir r. q u r c miny n l r d . III~II)pi:tuw~.mtd mu^ h h.~mIw~\it.: The )#sly~Ii%lmctiw pmt was thst a t the most critically complex point of the reaction-the transition state-everything seems to mova too quickly. One could hack up and review the process but, as in a magic trick, it seemsto flash by as quickly as before. This module also includes a number of simulation experiments in which the student interacts with the computer by controlling some of the variables. These simulations, as well as similar ones on other disks, provide compelling evidence of the computer's potential far innovative and enriching teaching. I t makes it possihle for the student to go through the many steps of an organic experiment quickly without actually being in the laboratory. The mechanisms of same of the reactions were perhaps treated i s too much detail, hut it is clear that this is the area where the computer shines. Approximately 10 of my 25 students interacted with Stanley Smith's eomputerbased program in "Organic Chemistry." Although the sampling is small, it represents diverse backgrounds and interests. Most of these students hope to transfer to four-year schools to complete the necessary requirements for pre-med, dentistry, engineering, or bioloev. the"* are older students -" Tv~icallv.
