. An Oraanic Svnthesis Program for Allied Health
,Chemistry Patrlck Flash Kent State Universlty-Ashtabula Campus Ashtabufa, OH 44004
' Most no&ommercial CAI programs dealing with functional group conversions in organic chemistry that have appeared in this Journal have been minicomputer- and textoriented ( 1 4 )or required expensive graphics terminals (58). The programs in one case were shown to be effective in helping students learn organic reaction chemistry (9). Recentlv a microcom~uterDroeram but it. . .. has also aoneared. .. too, Li text-oricnted ( l o ) .This paper describes a oriented nrorram. Orranic Reaction Chemistrv (ORCJ.that was writtkn i o aid alced health students withlearning and codifying organic reactions.7 The results of a preliminary test of the effectiveness of the program have also been suhmitted for publication in this Journal. ORC was written to supplement the textFundamentals of General, Orzanic, and Biochemistrv bv John Holum and covers the organicreactions in chapters il-17. The program is menu driven for easy student use. From the main menu, the student can select either of two operating modes: the drill function (Mode I) or the search function (Mode 11). In Mode I, a submenu allows selection of which functional group or groups to work with and whether to drill on supplying the reagents or drawing the product structure. When used in mode I-A, the program draws reactant and product molecules. I t then draws a reaction arrow and places a possible reagent over the arrow. The student uses the Avvle's horizontal arrow kevs to chanee the reagent visible o;& the arrow, stepping forward or bickward &rough the list of reagents until one that will effect the change is visible. The reagent selected is then entered by pressing the E (for enter) key. The program will accept any one of up t o four Chemical graphics via NUDRAW by Victor Bendall, Eastern Kentucky Univ.
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Br2 CH$H2CkCH2
CORRECT
correct answers for a problem. If the entered reagent is correct, the program writes the word "correct" below the arrow and waits For a press of the space bar before generating the next problem. If the answer is incorrect. the vromam writes "iicorrect" below the arrow and asks if the-student would like to try again. An affirmative answer results in the previous prol~lembeing regenerated while a negati\.e answer results in acorrect reagrnt beingdrawnover the arrow. After a second incorrect answer, the program automatically draws a correct reagent over the reaction arrow and waits for a press of the space bar before generating the next prohlem. A sample screen dump from a type LA problem appears in Figure 3. There are 57 reagents in the data set for mode LA. They follow the order: inorganics first, in alphabetical order, and then organics in the order of increasing numbers of carbons, hydrogens, etc. A list of the reagents can he found in the table. If the student using the pro&am is unfamiliar with the reagent set, I have found that i t is quite helpful to ~ o sthe t list of reagents where it is easily seen (for example, taped to the top of the monitor). The student can then locate the desired reagent on the list before using the arrow keys to place it over the reaction arrow. With mode I-B, ORC draws one of the 70 starting materials on screen. I t then draws the reaction arrow and a reagent over the arrow. Finally, the program draws a list of numbered chemical fragments such as CH2, CH3, C=C, etc., a t the hottom of the screen. The student must construct the product molecule by selecting the proper sequence of chemical fragments. As each numbered arouv - . is selected and then entered with the return key, the corresponding fragment appears on the product side of the reaction arrow. The fraements automatically align in a linear manner to generate tf;e product molecule. Certain conventions must be followed when entering product molecules. Most of these are standard to organic chemistry and those that are not are clearly spelled out in the directions subroutine within ORC. A screen dump of a mode I-B problem is shown in Figure 4. As with mode I-A, the student has two tries to get the correct answer with mode I-B. He can opt not t o try twice and always receives the correct structure a t the end of the prohlem. Pressing the space bar again triggers the next problem. The student can switch between mode I-A and I-B by pressing the ESCAPE key a t the beginning of a problem. Reagents for Organlc Reactlon Chemlstq (ORC) Program 1. 2. 3. 4. 5. 6. 7. 8.
Flgwe 3. Screen dump of a Mode l-A problem,
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0
LiAlH4-H30+
I1
CH3CH
INCORRECT TRY AGAIN?(Y/N)
0
II
CH3COCI
GROUP? E l.H
2.CH
3.CH2
6.C1
7.0
8.S
11.S03H
31. NR
0 II 12.C
32. ERA
4.CH3
5.Br
9.Na
10.N02
OH
13.h~
33. SCRN
Figure 4. Screen dump of a Mode 1-6 problem.
238
Journal of Chemical Education
CH3 14.h
Ag+ Br2 Bre/A Br2/FeBr3 CI2 CI2/A C12/F&ls Cu2+10H9. HBr 10. HCI 11. HNOI/HISOI 12. H2/Pd 13. H20/H2SO1 14. HsOt 15. H2SO4114O0C 16. H2SO4/170'C 17. i2 18. KMnOl 19. K2Cr,0,/H30+ 20. LI/NH3/HsO+ 21. LIAIHI/H~O+ 22. NH, 23. Na 24. NaOH 25. NAOH-Ha
This action takes the user to a submenu from which the other drill mode is accessable or from which the student can access mode 11, the search mode. While in the drill mode, the program keeps track of all student responses. When the student finally leaves this mode, the program prints a summary of results. The four categories listed are: problems correct on the first try, problemicorrect on the second try, problems with no second try, and problems missed on both tries. The program also generates a coded number a t the end of the drill mode. This number, when decoded by the professor,indicates how many total problems the student has tried in a session with the program. With mode I1 the student can search to total data set for reactions involving specific reactant functional groups, product functional groups, or reagents. For example, the btudrnt can nearrh f&nlfreactionein whirh an nlrohol is the stsrtinr material or do a more limited search for reactions in which an alcohol is the reactant but only aldehydesfketones areproducts. As another example, the student can search for any reactions using dichromate as a reagent. Mode I1 is also menu controlled and needs no external prompts or directions. However, i t does require the list of reagents for a reagent search. When finished with the search mode, the student can switch back to the drill mode or quit. Some of the advantages of Organic Reaction Chemistry over previous programs are that all the organic reactions are on one disk, the student can work on supplying both product structure and reagents, the program is graphically oriented, the search mode allows linking reactions across chapter boundaries, the summary a t the end of the drill provides quantitative feedback, and, finally, with mode I-B the student must actually construct the product molecule and just look a t a flash card and mentally say, "Yes, I know the structure of that product." Organic Reaction Chemistry is written in Applesoft Basic and occupies 18K of memory. An additional 1K of memory is occupied by the binary tables of reactants and reagents. The program runs on an Apple IIe or 11+ with lower-case chip. There are 150+ reactions in the data set. The program is currently available by sending a blank disk in a prepaid envelope and $4.00 to the author. The program has been submitted to Project SERAPHIM and may be available through them in the future. Acknowledgment . I would like to thank the National Science Foundation (the RISE program, grant SED 8020159) for the funds that were used to pirchas; the Apple computer system on which the program was written and studept-testad.
Comput Program tor Allocation ofirganic &litatin Analysis Unknowns
the students may use IR and NMR and have access to spectral libraries, they are required to perform chemical classification tests and nreDare two derivatives to confirm each idcntification. ~ h ; unknowns . are l i m i t d to those found in the tablesofthe CRCHondbookforIdrntificotionof. Ormnic Compounds, 3rd edition. The selection of appropriate unknowns for relatively laree numbers of s t u d e n & ~ t y ~ i c a l50-70 ly per semester) had hecome a somewhat tedious task, particularly in terms of making certain the class received a-random group of unknowns rather than the same combinations of compounds year after year. To this end we have developed a computer program written in IBM BASICA to generate a random group of four unknowns for each student. This program has been successfully used for the last four semesters a t Illinois State University. The program consists of a file of possible compounds belonging to the six classes mentioned previouslv. in . Tvpicallv .. less-than one-half hour the programkill generate a group of four compounds (two singles and a mixture) for each student. These must fulfill the following specifications: (1) no student will receive two compounds having the same functional group (aldehydes and ketones are considered to have the same functional group); (2) each student will receive a t least one solid and one liquid; and (3) the mixture will be separable by acid-base extraction techniques. The total nrozram consists of five individual seements . that are automatically loaded into the computer and selected from a simple menu (INTRO). The SETUP selection creates the file of unknown compounds, and allows for changes in this file. ALLOCAT chooses two single "unknow&" and an "unknown mixture" containing t a o compounds per student. The PRINTOUT selection is also menu-driven and produces a variety of printouts. The complete compound file and a listing of the compounds by a selected functional group can he &wed on the monitor with the selection SCREEN. The fifth program. DOCV,contains general information about the entif.e program and alisting of the variables used in the other four programs. The "unknowns" are randomlv selected from a source file that currently contains approximately 200 compounds classified bv the six functional zrouns " . mentioned nreviouslv. Since many compounds have more than one functional group, compounds containing halo, alkoxy, cyano, nitro, and vinyl substituents are also in the file. Aromatic, aliphatic, cvclic. and heterocvclic structures appear as well. The first sk~ectionof the SETUP program asksthe user ten questions about each compound being placed in the "unknown" file. The second selection allowsadditions, corrections and deletions; consequently the compound file can readily be changed to reflect the availability and needs of a particular school. Error checks are present t o catch many predictable entry errurs.After new compounds have beenadded,a printout of the new material ran be obtained. Figure 5 shows the information entered for a typical compound.
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Ann L. Pontius and Michael E. Kurr Illinois State University Normal. IL 61761
At Illinois State University organic chemistry students perform specific experiments stressing a variety of important synthetic reactions and techniques for the first half of the semester, and then devote the last half (which entails about 14 3-hour lab periods) to organic qualitative analysis. During this time each student is given two single "unknowns" and a mixture of two components to characterize and identify. We have chosen to limit the unknowns to six classes of com~ounds(aldehvdes. , ketones. alcohols..nhenols. carboxylic acids, and m i n e s ) , which are quite readily characterized by both chemical and spectral methods. Though
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Figure 6. Instructor listing of mixture compound data. Volume 64 Number 3 March 1987
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