1 * Prof. FAHMY A.F.M. & ** Prof. LAGOWSKI,J.J. * Faculty of Science, Department of Chemistry,Ain Shams University, Abbassia, Cairo, Egypt ** Department of Chemistry and Biochemistry, the University of Texas at Austin, TX Website: 42nd IUPAC Congress Chemistry Solutions, Glasgow,UK Aug. 2009

2 Introduction:  In the last ten years, we have designed, implemented, and evaluated the systemic approach to teaching and learning chemistry (SATLC) (1-3).  Also we have designed a new type of objective test in chemistry based on systemics (4).  This Lecture focuses on the use of the systemic approach to teach problem solving in chemistry at the university level (Tertiary level).  Traditionally, problem solving (TPS )as a process has been presented to students by the teacher doing problems, in effect showing them how to do certain types of “hard” problems, and then assigning similar problems for students to practice. Students will reach conceptual understanding through sufficient practice of problem solving (5).

3  By repetitive practice on this kind of approach to problem solving: Many students may develop speed and accuracy for routine problems, but they fail to develop their ability to reflect on what they have done or how to adapt this to solving new—different—problems.  Students solve these routine problems as snapshots without any framework connecting their ideas or even solutions to the context of the problem.  This approach stresses linearity in problem solving, (LPS) and linear thinking; as such, it relies on memorization.  Traditional (Linear) Problem Solving (LPS) is a useful tool to help teachers examine recall of information, comprehension, and application.

4  Systemic problem solving (SPS): Helps the students to connect Issues, Facts, and concepts.  E.g. Type of Chemical bonding in compounds, and its relationship to stereochemistry, gives rise to certain physical properties (e.g., dipole moment, IR, UV, NMR, MS,…), as well as chemical properties  SPS can challenge students and probe higher cognitive skills like analysis, synthesis, and evaluation.

5 LPS SPS TYPE (1): AB BC CD (?) (1 (2 (3 AB DC (?)

6 TYPE (2): DC A B (?) B A D C TYPE (3): AB CD (?) AB DC

7 GENERAL PRESENTATTION OF SYSTEMIC PROBLEMS (SP) Monitor the changes in Physical and/ Or Chemical Properties Problem (3) ? Problem (2) ? Problem (4) ? Problem (1) ? Atom, Compound, Complex

8  Sp.1 Compound C 4 H 8 (A) exists in two geometrical isomers reacts with dil. alkaline KMnO 4 to give C 4 H 10 O 2 (B).Compound (B) reacts with PBr3 to give vicinal dibromo Compound C 4 H 8 Br 2 (C). The dibromo derivative (C) reacts with alco. KOH to give C 4 H 6 (D). 1) Write the names, and Draw the structural formulas of Compounds (A D). 3) What are the types of hybridized in Compounds (A ), (D). 4) Give the systemic clockwise Chemical relations between Compounds in a systemic. (A D) 2) Draw the stereo isomers of Compounds (A C).

9 5) Monitor the changes of the following items in this systemic. i) Functional groups. ii) Reaction type for each step. iii) Systemic Change in hybridization of (C2-C3) when we move from compound (A to B- C-D). iv) Systemic Change in stereoisomerism when we move from compound (A to B-C- D). v)Systemic change in IR Bands when we move from compound (A to B-C- D). vi) Systemic change in 1H. N. M. R. signals, when we move from compound (A to B-C- D).

10 A 1) 2 - Butene : H H I I CH 3 - C = C - CH 3 2, 3- Dihydroxy butane: CH3 – CH - CH - CH3 I I OH OH 2, 3-Dibromobutane : CH 3 – CH - CH - CH 3 I I Br Br 2- Butyne: CH 3 – CH  CH - CH 3 CH 3 H H HH Z – 2- Butene E – 2 - Butane

11 ( DL ) CH 3 H OH HO H CH 3 HOH H HOH H OH CH 3 (meso) CH 3 H Br H H CH 3 H Br H CH 3 Br H CH 3 (meso) ( DL )

12 H H 3) CH 3 - C = C - CH 3 (A) 3 2 (SP2) CH 3 - C  C - CH 3 (D) 2 3 (SP) CH 3 – CH = CH - CH 3 dil. alk. KMnO 4. CH 3 -CH – CH - CH 3 l l OH CH3 – C  C - CH3 alco. KOH/ CH 3 - CH – CH- CH 3 l Br Br heat PBr 3 H2 / Pd/C

13 5) i) Change in the Functional Groups: (A) C = C ( B) 2CH-OH (D) C  C (C) 2 CH-Br ii) Change in the reaction types: CH 3 CH = CH - CH 3 (Addition.) CH 3 – CH – CH –CH3 OH OH Subtistitution) CH 3 – C  C - CH 3 ( Elimination ) CH3 – CH – CH – CH3 Br Br (Addition.)

14 ( iii) Systemic Change in hybridization of (C 2 - C 3 ): CH 3 – CH – CH – CH 3 OH (Sp 3 ) 2 3 Sp 2 Sp 3 CH 3 – CH = CH – CH 3 (Sp 2 ) 2 3 (SP SP2) Conservation of hybridization CH 3 – CH – CH – CH 3 Br Br (Sp 3 ) 2 3 Sp 3 Sp CH 3 – C  C – CH 3 (Sp) 2 3

15 iv ) Systemic Change in the stereoisomerism :  CH 3 – CH – CH – CH 3 OH Optical Change CH 3 – CH = CH – CH 3 Geometrical Conservation Of Chirality  CH 3 – CH – CH – CH 3 Br Br Optical Loss of CH 3 C  C – CH 3 No Stereo Isomers Geo. Opt. Creation of Geo. Chirality

16 CH 3 – CH – CH – CH 3 OH (  OH ) CH 3 – CH = CH – CH 3 (  C = C ) CH 3 – CH – CH – CH 3 Br Br (  C– Br ) CH 3 – CH  CH – CH 3 (  C  C ) (V) Systemic Change in the IR bands:

17 vi) Systemic Change in the 1HNMR : CH 3 – CH – CH – CH 3 OH CH 3 –CH = CH – CH 3 CH 3 – CH – CH – CH 3 Br Br CH 3 – C  C – CH 3 Appearance Of (CH – o-, and OH signals) Appearance of olefin Proton signals Disappearance of OH Signals Disappearance Of (H – C – Br Signals

18 SYSTEMIC PROBLEM SOLVING METHODOLOGY SYSTEMIC PROBLEM SOLVING METHODOLOGY P1P1 P3P3 P2P2 P4P4 SP P1P1 P3P3 P2P2 P4P4 √?√? ? ? ? (1) Stage ?? ? ? P1P1 P3P3 P2P2 P4P4 SP √ ? ? √ Stage (2) Stage (3) P1P1 P3P3 P2P2 P4P4 SP √ ? √ √ Stage (4) (SP 3 ) P1P1 P3P3 P2P2 P4P4 SP √√ √ √ SP-F) ( SP 4 ) ( SP-2) ( SPO)

19 By using (SPS), we expect from our students in organic chemistry to: - Produce systemic solutions for any complex chemical problem. - Enhance their problem solving ability. -Monitor the changes in the prediction of physical and chemical properties of different kinds of compounds obtained from the same or different kinds of problems. -Make maximum connections between, compounds, and their properties. - Recognize their own cognitive level in chemistry by problem solving. -Recognize the patterns of chemical and physical changes via problem solving.

20 References: 1- Ameen F. Fahmy, J. J. Lagowski., The Use of Systemic Approach in Teaching and Learningfor 21st Century, J pure Appl. 1999,71(5), [15th ICCE, Cairo, August 1998]. 2- Ameen F. Fahmy, J. J. Lagowski, Systemic Reform in Chemical Education an International Perspective, J. Chem. Edu. 2003, 80 (9), Ameen F. Fahmy, J. J. Lagowski Using SATL Techniques to Assess Student Achievement, [18th ICCE, Istanbul Turkey, 3-8, August 2004]. 4- Ameen F. Fahmy, J. J. Lagowski,Systemic Multiple Choice Questions (SMCQs) in Chemistry [19th ICCE, Seoul, South Korea, August 2006]. 5- Hollingworth, R, Chemical Education Journal (CEJ),2001,.5(.2 ),