Organic Reaction Chemistry P. Flash and V. Bendall, COMPress, P.O. Box 102, Wentworth. NH 03282
Summary Ratings: Reviewer Category EBJB of Use
Hardware: Apple II family (except the II+) Components: 1 disk, 1 back-up disk, and User's Manual Level and Subject: Organlc chemistry, sophomore level Cost: $60 each
Organic Reaction Chemistry is actually six different programs which allow the user t o oractice: (1) . . identifvinn . - functional groups, (2) supplying the missing reagent necessary to complete a given reaction, (3) deducing the product of a given reaction, (4) ascertaining whether a given reaction will go and identifying the functional group produced, and also to (5) search the reaction data base for functional group conversions and (6) search for the utility of a particular reagent. In "Functional Grouo Names" a structure is presented on the sereen and thestudent is asked to identify it asoneof the 25 functlmal groups contained in the data base by typing in the appropriate name. These groupings were delineated in the on-screen directions for the program. I t was of interest to me that some additional names were judged as correct, e.g. mercaptan in addition to thi01 and olefin as well as alkene. but ammonium salt was not ludged appropriate for amme salt The common funct~onnlgroups were well represented but some groups that are usually not encountered early in most courses (where I would think that this program might he most helpful) also appeared. Examples of these are hemiacetals, acetals, ketals, and hemiketals. The program was easy to use, but I found having to use the left
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Student Reaction: arrow key rather than the delete key in correcting typing errors to be annoying. The data base is apparently somewhat limited since the same structures tended to appear frequently. This limitation applies to the other programs as well. This program works reasonably well hut is, in my opinion, of limited use in a course which proceeds by the sequential introduction of functional groups. T h e second program, "Supply t h e Reagents", is potentially of much greater utility. In this program the student can select, from a list of functional groups starting with alkanes and proceeding through amides, those groups with which he is familiar. Reactants and products are shown and the student is asked to select a reagent (from a list shown on the lower oart of the screen) w h i ~ hwill indure t h e transformation shown. After the selection 1s made, prexring the "J" ljudgel key elicitn a currect or inrorr e d judgement from the computer. In the event that a response is incorrect the student is invited to try again. A second incorrect answer elicits a display of the correct answer. This oromam .. is well conceived and wwku well for the reactions in the data base. It is unfortunately hadly tlswed in the following manner. Renetiuns which are not normally encountered as the common synthetic procedure, hut which would proeeed rapidly and cleanly, are identified by the program as not proceeding. For example, the dehydrohalogenation of l-ehloropropane to propene is assumed to occur if KOH ~~~
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and alcohol is used, hut not NaNHz. NaNH2 does, however, form alkynes from dibromides. HCI will apparently form the n-propylammonium cation from n-prapylamine, but HzS04 and water will not. NaNH2 will not induce aldol condensations. I t was also interesting that HzSO* a t 140 degrees will not dehydrate primary, secondary, or tertiary alcohols, hut a t 170 degrees the reactions go readily. Benzene will apparently not sulfanate with H2S04at either 140 or 170 degrees but will with HtSOn/SOs. The next program, "Supply the Product", is slightly more complicated to use on first encounter. A student first selects a functional group, or groups, upon which he wishes to practice and the program generates reagents above the reaction arrow. The student is to respond by creating structures from a list of molecular fragments shown on the lower portion of the screen (e.g., CHa 0 , and H would have to be selected sequentially to respond with the methanol structure). This construction is a bit awkward a t first but rapidly hecomes routine with practice. In my opinion this program is the most useful of the six. In "Reaction Quiz" the student selects a reagent from a List shown on the lower portion of the screen, t h e program cycles through reactants containing various functional groups, and the student is to respond by answering Y or N (yes or no) as to whether a reaction will proceed. When a correct response of Y is entered the program asks for the functional group of the product to be
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IReviewed
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Sublecr Matter Content
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Reviewer Computer Learning Packages P. Flash and V. Bendall, Organic Reaction Chemistry J. A. Weyh, J. R. Crook, and L. N. Hauge, Chemical Reactions. Reactions in Aqueous Solution, and Oxidation Reduction Reactions
Books
J. H. Hargis
170
Wilmon B. Chipmon Robert J. Balahura William F. Colman
172 173
Karl F. Kumli
174
George B. Kauffman
175
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Andrejus Korolkovas. Essentials of Medicinal Chemistry, Second Edition Raymond B. Seymour and Charles H. Fisher, Profiles of Eminent American Chemists Monographs
Journal
of Chemical Education
entered. A return then brines on the next reactant for ronsideration. A correct response of N also causes the program to proceed to the next problem. This is good practice and fun hut unfortunately some reactions are adjudged to he "no reaction'' that actually would proceed. For example thiols can supposedly be oxidized to disulfides with I2 hut not with BrZ.Propene gives "no reaction" with Brz and heat. KMnO4 alledgedly will not react with thiols or disulfides, a hemiacetal will not react with Li, aldehydes do not react with Brz and heat, and alcohols do not react with C1ziJ?eCls. The other major problem is that when reactions are repeated (as mentioned above this happens frequently) or when an insignificant change is presented (e.g., propanoie rather than ethanoic acid is treated with a oartieular reagent) the "return for nest reaction" is inoperative and the student must proceed through the S or N responses before he may proceed. The last two programs, "Reagent Search and Reaction Search". allow the data hase to he searched for reactions caused by a particular reagent and for reagents which would cause a particular functional group conversion, respectively. Both of these programs are well designed and potentially of use hut are limited by the small data base from which they feed. Far example no reactions converting phenols to esters nor nitriles to amides are listed, nor are reactions converting organometsllies to alkanes, or alkvl halides to aromatics. The doeumentation of the proflams is succinct and clear but is, in reality, unnecessary l m a u ~ ethe programs contain clear directions and are menu driven and are easy to use. All in all the Organic Reoclion Chemistry package is well conceived and could become a valuable practice and drill instrument if the data hase were extensively expanded. J. H. Hargis Auburn University Aubum. AL 36849 RevIew II Organic Reaction Chemistry by Flash and Bendall is an instructional oackaee " designed to help all of the students m a onesemester organic chemratry course tu learn common organic reactions and to organize their knowledge of these reactions. The saftware also can he used by students in a twosemester organic chemistry course, either to learn reactions or as a review of reactions knowledee and as a helo in oreanizine " " about reartrona. It is suitable for both rhemistry majors and nonmajors a l r w they have heen exposed to a moderote numher of chemlral reactions and a large numher of functional groups. This means that the use of the software must occur somewhere late in a course. The one-disk package is copy protected and an archival copy is provided along with a 16Dare ~.manual. Theaualitv,ofthe documentat ~ o nis excellent (A minor problem rould have beenavoided hy havmg the part softhe program bear the same numbers as the corresponding sections of the manual.) No problems were encountered by students in using the programs, even without the documentation. The internal prompting and inputlerror handling are of very high quality. Audible responses to answers may he used or eliminated a t the option of the user.
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COMPress's copy protection system is controversial. The system defeata any of the usual copy-protection breaking techniques and hence the programs are neither listable nor modifiable. This means that it is not possible to change the list of reactions or the list of reagents to accommodate the software to particular local circumstances. This is a major problem with this particular promam. (Other COMPress software allows the user enter or mudify data files while still maintaining the same level of ropy protrc-.-..., Although advertising, flyers and the documentation indicate that the software is usahleon the Ande II'sswellasthe A ~ d e l I e and IIc, we &re not able to run i t on the Apple II+. Since the copy protection prevented us from examining the code we contacted COMPress and they subsequently acknowledged that the programs would not run on the IIf, hut run only on the IIe and IIc. (Since we did not have a IIc, we did not check whether the software would run on a IIc.) Organic Reaction Chemistry consists of six units: (1) "Functional Group Names", (2) "Supply the Reagents", (3) "Supply the Product", (4) "Reaction Quiz", (5) "Reagent Search", and (6) "Reaction Search". The option to return to the main menu a t almost any point in the program is available. (Same students felt that they would prefer not to have to return to the main menu to restart a narticular unit.) "~uncAonalGroup Names" is a drill and practice unit for naming 25 common functional groups. The name of the functional group must he spelled correctly; a wrong answer produces the correct answer after the ermr is noted. Even the better students Learned something from this unit about recoenizine a functional moun. in a molecule. However. several minor oroerammine hues detracted from this unit. (It is disconcerting to learn that while CHISH end CH.,CHrSH are throhCH3CH2CH2SHmay be an amine salt, an aeetal, an alkene, a disulfide, or a thial.) The selection of functional groups seemed to repeat in a somewhat less than random manner. Whether this was a poor random numher eenerator or a desirable use of repetition in teaching is not obvioussince the code cannot be examined. "Supply The Reagents" is a unit in which students are asked to select the correct reagent to convert a selected functional group to another functional group. The visual displays of starting material and product are excellent. The list of reagents includes 80 reagents, and must he "flipped" through one by one, although they are organized logically and the organization is made explicit in both external and internal documentation. Flipping through the reagents takes time, and it is not immediately obvious that you start in the middle of the list unless you consult the written documentation. Possihlva card listine the reaeents in order would hpa useful aid.u~nswe
