1. SYSTEMIC APPROACH TO TEACHING AND LEARNING HETEROCYCLIC CHEMISTRY (SATLHC) 2008 A. F. M. Fahmy, M. A. El-Hashash Faculty of Science, Department of Chemistry and Science Education Center, Ain Shams University, Abbassia, Cairo, EGYPT E-mail:fahmy@online.com.eg W.A.Abduo National research Center,Cairo,Egypt

2. The linear representation (1a) Vis systemic representation (1b) of concepts. Fig: 1a concept Fig: 1b concept

3.  Systemic Teaching Strategy: we started teaching of any unit by Systemic diagram (SD0) that has determined the starting point of the unit, and we ended with a final systemic diagram (SDf) and between both we crossover several Systemics(SD1,SD2,...) SD0 SDf SD2 SD1 Fig (2): Systemic teaching strategy

4. SATLHC Pure Applied - Synthesis - E-Substitution - Nu-Substitution - Addition - Cycloaddaition - Ring Opening - Het. Int. Conversion - Pharmaceuticals - Food Additives - Plant growth regulators - Insecticides - Herbicides - Corrosion Inhibitors - Super conductors. - Dyes - Photographic materials etc..) [LATLHC] Z Het. X Z Y Z E Z F X,Y,E,F [SATLHC] Z = N, O, S (Functional Groups) Z Het.

5.  Application of SATL In Heterocyclic Chemistry:  A course on heterocyclic chemistry using the SATL technique was organized and taught to 3rd year students at Ain Shams University. A portion of the one-semester course (10 lectures, 20 hours) was taught to students during the academic years.  1999/2000, 2000 / 2001, and 2003 / 2004

6.  Linear VS Systemic Study in Heterocyclic Chemistry:  Linear study in heterocyclic chemistry means servay study on the reactivity of the heterocycles to give products in a separate chemical reactions (Alkylation, acylation, Nitration, Sulphonation, formylation, …..).  Systemic study in heterocyclic chemistry means servay study on the reactivity of both heterocycles and substituents and their all possible chemical relations.

7. Heteroatom: [(Z) = NH, O, S] Substituents:[(G) = R, - CH 2 - X, - -CH 2 - OH - NH 2, - CHO, - COR, - COOH] G Reactivity of the Nucleus Reactivity of the Substituents Z

8. Figure 3: summarizes comparative reactivites of the five membered heterocycles as model heterocyclic compounds, and their possible relations.

10.  The diagram (4) represents the reactivity of heterocyclic nucleus, and gives the linear separated chemical relations between (pyrrole, furan, thiophene), and their compounds.  We use heterocyclic chemistry to illustrate, again, how a subject can be organized systemically. SD1 summarizes the comparative reactivities of both heterocyclic nucleus and substituents.

12.  In the systemic diagram (SD1) there are unknown chemical relations (1-7) between heterocyclic compounds. These relations will be clarified later during the study of pyrrole, furan and thiophene.

13. ASSESSMENT – I ON SD1 ASSESSMENT – I ON SD1 QI) Draw systemic diagrams illustrating the chemical relations between compounds in each of the following sets.

14. A I - 1

15. QII) Complete the following systemic diagrams: A II - 2

16. Reactions of pyrrole, and Pyrrole compounds(asExample) I-Pyrrole: (Prerequisites SD1)  We can summarize the reactions of pyrrole in the following diagram (Fig. 4).

17.  The diagram (Fig. 4) represents the reactivity of (pyrrole nucleus), and gives the linear separated chemical relations between pyrrole and its compounds.  We can illustrate the chemical relations in (Fig. 4) systemically by modification of SD1 to SD2 (Z = NH):

18.  Systemic diagram (SD2) shows know chemical relations between pyrrole and its compounds. We have the unknown chemical relations between pyrrole compounds (1-8), and should be clarified during the study of pyrrole compounds.

19.  After Study of pyrrole compounds [G = R, CH 2 OH, CHO, RCO, COOH, NH 2 ): We can modify (SD 2 to SD 3) by adding chemical relations (1 – 7).

20. ASSESSMENT – II ON SD3 ASSESSMENT – II ON SD3 QI) Draw systemic diagrams illustrating the chemical relations between compounds of each of the following sets: (clockwise) N H N N H COOHCHO,,1- H N H,,, NO 2 N H COOH N H CHO N H 2- H HH H N,,, NN N 2 Ph N COONH 4 COOH 3-

21. A I - 1 N H N H CHO N H COOH aq. alk. 200 o C heat KMnO 4 i)DMF, POCl 3 ii) aq. Na 2 CO 3

22. QII) Complete the following systemic diagrams: 1- N H COOH Ac 2 O- 10  C AcONO 2 / curtius rearrangement SOCl 2 200  c heat NaN 3............................ 2- N H N H N H DMF, POCl 3 aqNa 2 CO 3 aq.alk. KMnO 4 CHO COOH......... Then give the systemic chemical relations in a list

23. A II - 2 N H N H aq. alk. KMnO 4 bromination COOH N H N H CHO Br NBS, THF Vap. phase decarbonylation i) DMF, POCl 3 ii) Na 2 CO 3 heat, 200  c Above chemical relations in a list: N H N H N H COOH CHO N H N H N H Br COOH N H N H N H CHO N H N H N H COOH N H CHO Br

24. QIII) Arrange the following compounds in the right places in the following (SD.): CH 3 N H N,, H N H CHO N, H N H COOH NO 2 CH 3 MgX LTA/ AcOH  Oxid alk. KMnO 4........

25. QIV) How can you make the following conversions: 1)Pyrrole to pyrrole -2-carboxylic acid. 2)2-Hydroxymethylpyrrole to 2-phenylazopyrrole. 3)Pyrrole -2-carboxylic acid to 2-bromopyrrole. 4)2-Methylpyrrole to pyridine. 5)2- Formyl pyrrole to 2-Nitropyrrole. 6)Pyrrole -2- Carboxylic acid to 2-aminopyrrole. A IV - 2 N H N H COOH PhN 2 N 2 Ph + N H N H CH 2 OH Diborane CH 3 Chromic acid A IV - 4

26. QV) Rearrange the compounds in the following SD to give correct chemical relations: N H COOH N H N H NBS/THF COONH 4 N H Br hydrolysis (NH 4 )2 CO 3 / 130  C Seald vessel Br 2 200  C heat AV) N H COOH N H N H NBS/THF COONH 4 N H Br hydrolysis (NH 4 )2 CO 3 / 130  C Seald vessel Br 2 200  C heat

27. QVI) Which of the following systemics are true and which are fals: A VI) a: (x); b: ( )c: (x); d: ( )

28. QVII) Put ( ) Infront of the correct systemics: A VI) a: (x); b: (x)c: ( ); d: (x) The systemic diagram represents the correct chemical relations between pyrrole and its compounds is one of the following:

29. 1- Heterocyclic derivative to another Hetercyclic derivative: Example: Systemic Teaching Strategies For Uses Of Heterocycles In Synthesis

30. 2- Aliphatic compound to another aliphatic compound via Heterocycle:

31. 3- Heterocycles to homocycles:

32.  Conclusion:  After the experimentation of SATLHC in Egypt we reached to the following conclusions: 1) SATLHC improved the students ability to view (HC) from a more global perspective. 2) SATLHC helps the students to develop their own mental framework at higher-level cognitive processes (application, analysis, and synthesis). 3) SATLHC increases students ability to learn subject matter in a greater context. 4) SATLHC increases the ability of students to think globally.

33.  References: (1) Taagepera, M.; Noori, S.; J. Chem. Educ. 2000, 77, 1224. (2) Fahmy, A. F. M.; Lagowsik. J. J.; J. Chem. Educ. 2003, 80, (9), 1078. (3) Fahmy, A. F. M., El-Shahaat, M. F., and Saied, A., International Workshop on SATLC, Cairo, Egypt, April (2003). (4) Fahmy, A.F.M., Lagowski, J.J.; Systemic Approach in Teaching and Learning Aliphatic Chemistry; Modern Arab Establishment for printing, publishing; Cairo, Egypt (2000). (5) Fahmy A. F. M., El-Hashash M., Systemic Approach in Teaching and Learning Heterocyclic Chemistry. Science Education Center, Cairo, Egypt (1999). (6) Fahmy A. F. M., Hashem, A. I., and Kandil, N. G.; Systemic Approach in Teaching and Learning Aromatic Chemistry. Science, Education Center, Cairo, Egypt (2000). (7) Fahmy, A. F. M.; Hamza M. S. A; Medien, H. A. A.; Hanna, W. G., M. Abedel-Sabour; and Lagowski; J. J.; Chinese J. Chem. Edu., 23 (12) 2002, 12, 17th IEEC, Beijing August (2002).17th IEEC, Beijing August (2002).