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A. F. M. Fahmy, M. A. El-Hashash National research Center ,Cairo,Egypt

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

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

3 Fig (2): Systemic teaching strategy
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,...) SD1 SD2 SD0 SDf Fig (2): Systemic teaching strategy

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

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 G Z Reactivity of Reactivity of the Substituents the Nucleus
Heteroatom: [(Z) = NH, O, S] Substituents:[(G) = R, - CH2 - X, - X, -CH2 - OH - NH2, - CHO, - COR, - COOH]

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

9

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.

11

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 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). N H i) DMF/POCl3 ii) aq. Na2CO3 Ac2O -10C AcONO2 PhN2 THF NBS red. (NH4)2CO3 130c Sealed Vessel CO2NH4 + - + - Br N2 Ph NO2 ii)HCl NaOH RMgX i) C6H5NSO3 i) RCONR2 ii) NaOAc COR SO3H R CH2OH Cl CHO H2/Rany Ni CH2Cl2 CH3Li / + CHCl3/base HCHO

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 H N R=CH3 (1) (3) CHO Cl ? Reduction Oxid. base HCHO 130oc CHCl3/ i)DMF/POCl3 ii) aq.Na2CO3 RMgX (2) (4) (5) Ac2O,-10oc AcONO2 + PhN2 N2Ph heat 200oC (8) R CH2OH NO2 Br SO3H COR` i) R`CONR2/POCl3 ii) NaOAc i) C6H5NSO3 ii) HCl CO2NH4 CH2Cl2/ CH3Li (NH4)2CO3 COOH NBS/THF (6) (7) + - Wolff/ Kishner red. SD 2 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 Vap. Phase decarbonylation
After Study of pyrrole compounds [G = R, CH2OH, CHO, RCO, COOH , NH2): We can modify (SD 2 to SD 3) by adding chemical relations (1 – 7). H N CHO Cl Oxid CH2O/ NaOH base CHCl3/ Alkylation RMgx Wolff- kishner red. Nitration Ac2O-10C AcONO2 + PhN2 R = CH3 Oxid., chromic acid heat 200c CH2OH rearang. Curtius red NO2 SO3H i) R`CONR2/POCl3 ii) aq. Na2CO3 i) C6H5NSO3 ii) HCl aq. alkaline KMnO4 i) DMF/poCl3; ii) aq Na2 CO3 (NH4)2CO3 hydro CO2NH4 COR` CHBr2 Diborane R=CH3 NBS,CHCl3 refulx (R= CH3) hydrolysis H2/Pd R= CH3 NaBH4 Ag2CO3/Celite LTA/AcOH,  CO2H N2Ph NBS/THF CON3 pyridne SOCl2/ NaN3 COCl NH2 bromination Br CH2Cl2 / CH3Li C H2-Rany Ni R KMnO4 Vap. Phase decarbonylation SD 3

20 ASSESSMENT – II ON SD3 QI) Draw systemic diagrams illustrating the chemical relations between compounds of each of the following sets: N H COOH CHO , 1- (clockwise) H N , NO2 COOH CHO 2- H N , N2Ph COONH4 COOH 3-

21 A I - 1 COOH aq. alk. heat 200oC KMnO4 i)DMF, POCl3 ii) aq. Na2 CO3 N
CHO COOH aq. alk. 200oC heat KMnO4 i)DMF, POCl3 ii) aq. Na2 CO3

22 QII) Complete the following systemic diagrams:
COOH Ac2O- 10C AcONO2/ curtius rearrangement SOCl2 200c heat NaN3 1- 2- N H DMF , POCl3 aqNa2CO3 aq.alk. KMnO4 CHO COOH Then give the systemic chemical relations in a list

23 Above chemical relations in a list:
aq. alk. KMnO4 bromination COOH CHO Br NBS, THF Vap. phase decarbonylation i) DMF, POCl3 ii) Na2 CO3 heat, 200c A II - 2 Above chemical relations in a list: N H COOH CHO N H Br COOH N H COOH CHO N H COOH CHO Br

24 QIII) Arrange the following compounds in the right places in the following (SD.):
CH3 N H , CHO COOH NO2 CH3 MgX LTA/ AcOH Oxid alk. KMnO4

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. N H COOH PhN2 N2Ph + CH2OH Diborane CH3 Chromic acid A IV - 2 A IV - 4

26 QV) Rearrange the compounds in the following SD to give correct chemical relations:
COOH NBS/THF COONH4 Br hydrolysis (NH4)2 CO3/ 130C Seald vessel Br2 200C heat AV) N H COOH NBS/THF COONH4 Br hydrolysis (NH4)2 CO3/ 130C Seald vessel Br2 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:
The systemic diagram represents the correct chemical relations between pyrrole and its compounds is one of the following: A VI) a: (x); b: (x) c: (); d: (x)

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

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) , 12, 17th IEEC, Beijing August (2002).

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