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

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

3. INTRODUCTION -After the wide spread of the systematization in various activities including, tourism, economy, security, education, health, security …etc, & -After globalization became 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. T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, b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. Table 1: Percentage increase in student scores. Percent increase in student scores Before interventionAfter intervention Linear questions 37.32 %49.53 % Systemic questions 21.19%90.29% Total 32.52%69.1% T hese results are statistically significant at the 0.01 leve l.

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) To understand 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) To synthesize systemic chemical relations between compounds of the same or different heterocycles. 5) To understand 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. - 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.  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.

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 Fig: 1b SA concept

10.  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. SD0 SDf SD2 SD1 Fig (2): Systemic teaching strategy

11. C-Heteroatom: [(Z) = NH, O, S]S] D-Substituents :[(G) = R, - CH 2 - X, - -CH 2 - OH - NH 2, - CHO, - COR, - COOH] G A-Reactivity of the Nucleus B-Reactivity of the Substituents Z [ A ][ B ] [ D ][ C ] SATL-HC [STS]

12.  A list of SATLC materials were produced in Egypt  e.g.: SATL General Chemistry for secondary schools. SATL Aliphatic, 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 Membered Heterocylic Compounds with One Heteroatom [ e.g:Pyrrole ] Five Membered Heterocylic Compounds with One Heteroatom [ e.g:Pyrrole ]  We can teach pyrrole in the general frame of five membered heterocycles with one heteroatoms. The students build up with their teachers the following systemic [SD1;Fig.3].

14. - The student convert SD1-SD2 BY replacing Z with NH to 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. The students can modify (SD 2 to SD 3) by adding chemical relations (1 – 8).This is the SDf of Pyrrole study.  After Study of pyrrole compounds (G = R, CH 2 OH, CHO, RCO, COOH, NH 2 ):

16. - 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. SA To Assess Student Achievement in Heterocyclic Chemistry

17. Why Systemic Assessment [SA]? SA is a highly 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. SA strategy converts assessment from linear bothering exams to enjoyable puzzle games by playing with systemic assessment diagrams. This will reduce exam anxiety. SA will 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 compou nds..

19. Systemic Assessment in Heterocyclic Chemistry [SAHC] [ eg; Thiophene chemistry] - 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]  (SMCQs) are choose of one systemic from a list of possible systemics.  Each systemic represents at least three chemical relations between three heterocyclic compounds.

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

23. Q2 : A) a: ( )

24. (a) ( ) (b) ( ) Q3:

25. (c) ( ) (d) ( ) Answer: a ( )

26. Q4: Answer: C (  )

27. Type[2]: Systemic True False Questions (STFQs)  (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.

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. Q) Arrange the following heterocyclic compounds in the right places in the following (SD): N H,, N H CHO CH 3 N H N, H COOH N H NO 2, Example: CH 3 MgX LTA/ AcOH  Oxid alk. KMnO 4........ Chromi c acid Heat 200  C

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) :

37. (A)(B)(C) CO(OAC) 2 AcNO 3 BuLi DMF/POCl 3, NaOAc Cu/Quinoline, D (CH 3 ) 3 B/I 2 CH 3 I/FeCl 3 Zn[Hg]/HCl CH 2 O/HCl (CH 2 ) 6 (NH 2 ) 4 /alc. P2S5P2S5 NH 3 (hn) K 2 Cr 2 O 7 /H 2 SO 4 Heat 200  C HNO 3 [conc.] CH 3 MgBr, H 2 O NaNO 2 /HCl NaN 3

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. (A) (B) (C) HNO 2 PhCO 2 H NH 3 (i) H 2 SO 4 / (ii) KOH Ph 3 P NOCl Q 2: 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] Synthesis of Triangular Systemic Chemical Relations TYPE: 5-A Requires student to synthesize systemic chemical relations between concepts, facts,,atoms or molecules,

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. Q5: Draw systemic diagram illustrating the possible chemical relations between furan and the following related compounds O,,, O CO 2 H OO Br COOHBr A5: OO Br 2 Cu/quinoline  heat 200 o c COOH Br 2 / dioxan -5 o C O O Br COOH

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:

51. Synthesis of Hexagonal Systemic Chemical Relations Type 5-D

52. Q7: Draw systemic diagram illustrating the systemic chemical relations between pyrrole and the following related compounds: A7:

53. Open Synthesis Of Systemic Chemical Relations Draw systemic diagrams illustrating the systemic chemical relations between any : – Four heterocyclic compounds. – Five heterocyclic compounds. – Six heterocyclic compounds. Type 5-D :

54. By using Systemic Assessment in Heterocyclic Chemistry, We Expect from Our Students: - Making maximum connections between different heterocycles, and their applications. - View heterocyclic chemistry from a more global perspective. - View the pattern of pure and applied heterocyclic chemistry rather than synthesis and reactions of heterocycles. - Systemic solutions of any chemical problems in heterocyclic chemistry (Analytic, Synthetic). - Synthesize the given target heterocyclic compound by making use of different synthetic strategies.

55.  SUMMARY:  In the linear classical approach we teach & assess heterocyclic chemistry as separate chemical reactions of the rings and the relationships between heterocyclic compounds are ambiguous; however in SATL-HC the students are able to do the the following chemical transformations: 1- Heterocycles to another heterocycles in a direct pathway :

56. 2- Three-membered to four-membered heterocycles via aliphatic compounds and vis versa:

57. 3- Heterocyclic derivative to another hetercyclic derivative: Example:

58. 4- Aliphatic compound to another aliphatic compound via heterocycle:

59. 5- Heterocycles to homocycles :

60. 6- Design synthesis of any target heterocyclic system via Retro-Synthesitic Analysis[RSA]: Synthesis of [IMIDES]

61.  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 & enthusiasm to learn HC in a greater context. 5) SATLHC increases the ability of students to think systemically. 6 ) SATLHC enhances the students mental skills towards building target heterocyclic systems via Retro-Synthetic Analysis. 4)SATLHC help students to view the pattern of pure and applied heterocyclic - chemistry rather than synthesis and reactions of heterocycles.

62. Research Group Prof. Dr. Hashem A. F. (Egypt) Prof. Dr. El-Shahat, M. T. (Egypt ) Prof.Dr. Medien, H( Egypt) ) Mrs. Said, A. (Egypt Prof.Dr. Hamza, S. A. (Egypt) Prof. Dr. Hanna, W. G. (USA) Prof. Dr. Lagowski, J. J. (USA) (Founder ) Prof. Dr. Kandil, N. G. (Egypt) Prof. Dr. El-Hashash, M. (Egypt ) Prof. Dr. Abdel – Sabour, M. (Egypt)

63.  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), 107 8. (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., El-Hashash M., “Systemic Approach in Teaching and Learning Heterocyclic Chemistry”. Science Education Center, Cairo, Egypt (1999). (5) 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). ( 6) Fahm,A.F.M. and Lagowski,J.J.;”Systemic assessment as a new tool for assessing students learning In Chemistry using SATL” methods [I]:Systemic True False [STFQs] and Systemic Sequencing [SSQs] Questions. AJCE. 2, (2)66-78(2012). “ (7) Fahmy,A.F.M. and Lagowski, J.J;“Systemic Assessment as a new tool for assessing students learning in chemistry using SATL-methods” [II] : Systemic Machining Questions[SMQ,s], Systemic Synthesis Questions[SSyn Q,s], Systemic Analysis Questions[SAnQ,s],Systemic Synthetic/Analytic Questions[ SSyn-An Q,s] as new systemic Questions. AJCE 4 (4) 35-55 (2014).

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