SY SYTEMIC ASSESSMENT AS A NEW TOOL FOR ASSESSING STUDENTS LEARNING IN HETEROCYCLIC CHEMISTRY

1. SYSYTEMIC ASSESSMENT AS A NEW TOOL FOR ASSESSING STUDENTS LEARNING IN HETEROCYCLIC CHEMISTRY A. F. M. Fahmy, Faculty of Science, Department of Chemistry Ain Shams University, Abbassia, Cairo, EGYPTE-mail:afmfahmy42@gmail.com Website:satlcentral.com 13Ibn Sina International Conference Hurghada,Egypt; 14-17 Feb.2015

2. If their is no Teaching Chemistry their is no Chemistry • Good chemistry teaching excellent chemistry research

3. INTRODUCTION • -After the wide spread of the systematization in various activities including, tourism, economy, security, education, health, security …etc, & • -After globalizationbecame a reality that we live. • -SATL became a must and Chemical Education Reform (CER) has gained a great importance internationally. • - SATL is a new way of teaching and learning, based on the idea that nowadays everything is related to everything globally. • -Students shouldn't learn isolated facts (by heart), but they should be able to connect concepts and facts in an internally logical context.

4. Taagepera and Noori (2000)tracked the development of student’s conceptual understanding of organic chemistry during a one-year sophomore course. They found that the students knowledge base increased as expected, • but their cognitive organization of the knowledge was surprisingly weak . • The authors concluded that instructors should spend more time making effective connections, helping students to construct a knowledge space based on general principles.

5. Fahmy,A.F.M.(Egypt),andLagowski,J.J.(USA)(1998) Suggested an educational process based on the application of “Systemics” named (SATL). • SATL-in Heterocyclic Chemistry was experimented successfully on the third year major chemistry students at Ain Shams University( 2004). • The result of the final exam: shows that students taught systemically improved their scores significantly after being taught by using SATL techniques.

6. Percent increase in student scores Before intervention After intervention Linear questions 37.32 % 49.53 % Systemic questions 21.19% 90.29% Total 32.52% 69.1% Table 1: Percentage increase in student scores. These results are statistically significant at the 0.01 level.

7. Difficulties in Learning Heterocyclic Chemistry By Traditional Methods HC can appear unattractive to some students and they find the following difficulties in learning: 1) To Remember the structural formulas of heterocycles and chemical properties related to this structure. 2) Tounderstand the systemic effect of heteroatom on the reactivity of both heterocycles and their functional groups. 3) To follow up the theoretical bases connected to the complexity of Heterocycles. 4) Tosynthesize systemic chemical relations between compounds of the same or different heterocycles. 5) Tounderstand the importance of heterocycles in their life's. 6) To Design Synthesis of new target heterocycles via RSA. 7)Fears of the subject can then be compounded by the complexity of heterocycles.

8. Why Systemic Approach to Teaching and Learning ? • - SATL helps students in the development of their mental framework with higher level of cognitive processes such as analysis and synthesis. - SATL helps learners in obtaining a deeper learning experience, improve their understanding, enhance their systemic thinking, and increasing their enthusiasm for learning HC. - SATL,will help students to understand interrelationships between concepts in a greater context and help them to build new systemic relations between hetrocyclic systems. • - SATL Helps teachers to teach and learners to learn.

9. What is the meaning of SATL? • - SATL Means arrangement of concepts or issues through an interacting systems in which all relationships between concepts and issues are made, clear up in front, of the teachers and learners. Fig:1a LA concept concept concept concept concept Fig:1b SA concept concept concept

10. SD1 SD2 SD0 SDf • Systemic Teaching Strategy:[STS] • - 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. Fig (2): Systemic teaching strategy

11. [STS] G Z B-Reactivity of A-Reactivity of the Substituents the Nucleus SATL-HC C-Heteroatom: [(Z)= NH, O, S] D-Substituents:[(G) = R, - CH2 - X, - X, -CH2 - OH - NH2, - CHO, - COR, - COOH]

12. A list of SATLCmaterials were produced in Egypt • e.g.:SATLGeneral Chemistry for secondary schools. SATLAliphatic, Aromatic, Green chemistry and Heterocyclic Chemistry for the University Level. • In this presentation: • - The SATL- 5-membered heterocycle(eg.Pyrrole ), and • - The systemic assessment in heterocyclic chemistry • will be illustrated.

13. Five MemberedHeterocylic Compounds with One Heteroatom [ e.g:Pyrrole ] • We can teach pyrrole in the general frame of five memberedheterocycles with one heteroatoms. The students build up with their teachers the following systemic [SD1;Fig.3].

14. Reduction Oxid. Wolff/ Kishner red. ? CHO N (3) H Cl N i)DMF/POCl3 ii) aq.Na2CO3 R=CH3 CH2Cl2/ CH2OH N N CO2NH4 N H CH3Li H (8) HCHO ? (NH4)2CO3 R=CH3 CHCl3/ base ? base (1) 130oc RMgX heat COOH N R 200oC N H i) R`CONR2/POCl3 ii) NaOAc N + PhN2 (4) (2) H ? ? + - i) C6H5NSO3 ii) HCl (5) N N2Ph N COR` AcONO2 ? H H Ac2O,-10oc N SO3H H NBS/THF ? N NO2 (6) H Br N SD 2 H ? (7) -The student convert SD1-SD2 BY replacing Z with NHto show the known chemical relations between pyrrole and its related compounds. -In SD2 We have the unknown chemical relations between pyrrole compounds (1-8), and should be clarified during the study of pyrrole compounds.

15. After Study of pyrrole compounds (G = R, CH2OH, CHO, RCO, COOH , NH2): KMnO4 R= CH3 aq. alkaline KMnO4 H2/Pd Oxid CHO N hydrolysis Cl Vap. Phase decarbonylation H (R= CH3) Ag2CO3/Celite N N LTA/AcOH,  NaBH4 CH2Cl2 / CH3Li i) DMF/poCl3; ii)aq Na2 CO3 CHBr2 CHCl3/ N N N base CH2OH H H H H2-Rany Ni CH2O/ R=CH3 R=CH3 150-200C hydro NBS,CHCl3 refulx NaOH N CO2NH4 Diborane H (NH4)2CO3 RMgx heat Alkylation 200c R N N CO2H + H PhN2 N H i) R`CONR2/POCl3 ii) aq. Na2CO3 + PhN2 H Wolff- kishner red. N NBS/THF i) C6H5NSO3 ii) HCl N2Ph H AcONO2 bromination N Ac2O-10C COR` Br N N SO3H H H H Nitration N NO2 H SD 3 R = CH3 Oxid., chromic acid The students can modify (SD 2 to SD 3)by adding chemical relations (1 – 8).This is the SDf of Pyrrole study.

16. SA To Assess Student Achievement in Heterocyclic Chemistry • - The aim of the systemic assessment of learners is • to introduce an efficient evaluation of the systemic- oriented objectives of the [SATL-Heterocyclic Chemistry] model. • - SA is an effective tool for assessing students meaningful understanding of heterocyclic chemistry topics in the tertiary level.

17. Why Systemic Assessment [SA]? SA isahighly effective new assessment strategy raising the level of students academic achievements, SA enhances systemic thinking. SA enhances the student ability to correlate between concepts with a reduced working memory. SAstrategy converts assessment from linear bothering exams to enjoyable puzzle games by playing with systemic assessment diagrams. This will reduce exam anxiety. SAwill convert students from surface to deep learning.

18. Linear Assessment in Heterocyclic Chemistry [LAHC] [eg;Thiophene chemistry]Q:Completet the following equations: . In the LA we ask our students linear questions . Eg:In this question we assess our students in the memory learning level in which the student may complete the 6-equations from his memory as separated chemical relations. But however, he couldn’t synthesize the chemical relations between Thiophene, and its related compounds and the chemical relations between Thiophene compounds.

19. Systemic Assessment in Heterocyclic Chemistry [SAHC] [ eg; Thiophenechemistry] - Draw pentagonal systemic diagram illustrating the possible chemical relations between Thiophene compounds in the chemical equations (1-6) -We assess our student at the synthesis learning level by answering the systemic synthesis question [SSynQ] of the Thiophene compounds and he discovers two other new chemical relations between compounds(7, 8).

20. Types of SA QUESTION We will illustrate five types of Systemic Assessment Questions, used in Systemic Objective Test (SOT ). 1-Systemic Multiple Choice Questions (SMCQs). 2-Systemic True False Questions (STFQs). 3-Systemic Matching Questions (SMQs). 4-Systemic Sequencing Questions (SSQs). 5-Systemic Synthesis Questions (SSynQ,s).

21. Type [1]:Systemic Multiple Choice Questions • (SMCQs)are choose of one systemic from a list of possible systemics. • Each systemic represents at least three chemical relations between three heterocyclic compounds. [SMCQs]

22. Put () in front of the correct systemic diagram : Q1: Answer: c ()

23. Q2: A) a: ()

24. Q3:

25. Answer: a ()

26. Q4: Answer: C ()

27. Type[2]: Systemic True False Questions • (STFQs)require a student to assess whether a systemic is true or false. This means that the student assess systemic relations between concepts, rather than concepts. (STFQs)

28. Q1:Which of the following systemics are true and which are false: (a) ( ) (b) ( )

29. ( ) (c) (d) ( ) Answer: a ()-b (X) – c (x)-d ( X)

30. Q2) Which of the following systemics are true and which are false: A) a: (x); b: () c: (x); d: ()

31. Q3: Which of the following systemics are true and which are false: A ) a: (); b: (x) c: (); d: (x)

32. Q4: Which of the following systemics are true and which are false:

33. Answer: True systemics are (b, d, f) ()

34. Type[3]:Systemic Sequencing Questions (SSQs) SQs: Sequencing questions require the student to position Molecule, or text or graphic objects in a given sequence. (SSQs):require the student to position Molecule , or text or graphic objects in a given systemic sequence.

35. , , , CHO N N N CH3 H H H CH3 MgX ........ ........ , COOH N N NO2 ........ H H LTA/ AcOH  Heat 200C Chromic acid ........ ........ Oxid alk. KMnO4 ........ ........ Example: Q) Arrange the following heterocyclic compounds in the right places in the following (SD):

36. Type[4]:Systemic Matching Questions(SMQs) Q1:Choose Heterocycles from Column (A) and Reaction Conditions from Column (C)to Construct the Systemic Diagrams in Column (B) :

38. A1:Answers in a triangular systemic chemical relations:[ 4 different answers as examples]

39. A2:Answers in a quadrilateral systemic chemical relations: [2 Different answers as examples]

40. A3:Answers in pentagonal systemic chemical relations: [2 Answers as examples]

41. Q2:Choose compounds from column (A) and reaction conditions from column (C) to build the systemic diagram in column (B):

42. Type[5]: Systemic Synthesis Questions [SSynQs] Requires student to synthesize systemic chemical relations between concepts, facts, ,atoms or molecules, Synthesis of Triangular Systemic Chemical Relations TYPE: 5-A

43. Q1– Draw triangular systemic diagram illustrating the systemic chemical relations between thiophene and the following related compounds: A1

44. Q2:Draw triangular systemic diagram illustrating the systemic chemical relations between the following five membered heterocyclic compounds: A2:

45. Synthesis of Quadrilateral Systemic Chemical Relations TYPE 5-B

46. Q3: Draw systemic diagram illustrating the systemic chemical relations between the following compounds: A3:

47. Q4: Draw systemic diagram illustrating the systemic chemical relations between the following compounds: A4:

48. Br2 COOH Br COOH O O heat 200oc Cu/quinoline D Br2 / dioxan -5oC Br O O , , , Br COOH Br O O O O CO2H Q5: Draw systemic diagram illustrating the possible chemical relations between furan and the following related compounds A5:

49. Synthesis of Pentagonal Systemic Chemical Relations TYPE 5-C

50. Q6:Draw systemic diagram illustrating the systemic chemical relations between the following compounds: A6: