SYSTEMIC PROBLEM SOLVING TO ASSESS STUDENT ACHEVEMENTS IN CHEMTSTRY BY & * Prof . FAHMY A.F.M. ** Prof . LAGOWSKI,J.J. * Faculty of Science, Department of Chemistry,Ain Shams University, Abbassia, Cairo, Egypt E-mail: fahmy@online.com.eg ** Department of Chemistry and Biochemistry, the University of Texas at Austin, TX 78712 E-mail: jjl@mail.cm.utexas.edu Website: www.satlcentral.com 42 nd IUPAC Congress, Glasgow, Aug 2- 7 (2009).  

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).

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.

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.

Linear VS Systemic problem Solving GENERAL STRATEGY FOR Linear VS Systemic problem Solving SPS LPS TYPE (1): A B D C (?) A B C D (?) (1 (2 (3

TYPE (2): D C A B (?) B A D C (?) TYPE (3): A B D C (?) A B C D (?)

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

Sp.1 Compound C4 H8 (A) exists in two geometrical isomers reacts with dil. alkaline KMnO4 to give C4 H10 O2 (B) .Compound (B) reacts with PBr3 to give vicinal dibromo Compound C4 H8 Br2 (C). The dibromo derivative (C) reacts with alco. KOH to give C4 H6 (D). 1) Write the names, and Draw the structural formulas of Compounds (A D). 2) Draw the stereo isomers of Compounds (A C). 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)

ii) Reaction type for each step. 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). 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).

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

( DL ) CH3 H OH HO (meso) CH3 H Br (meso) ( DL )

dil . alk. CH3 - CH – CH- CH3 heat 3) CH3 - C = C - CH3 (A) 3 2 (SP2) CH3 - C  C - CH3 (D) 2 3 (SP) CH3 – CH = CH - CH3 dil . alk. KMnO4. CH3 -CH – CH - CH3 l l OH OH CH3 – C  C - CH3 alco. KOH/ CH3 - CH – CH- CH3 l l Br Br heat PBr3 H2 / Pd/C

(A) C = C (B) 2CH-OH (D) C  C (C) 2 CH-Br 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: CH3CH = CH - CH3 (Addition.) CH3 – CH – CH –CH3 OH OH Subtistitution) CH3 – C  C - CH3 ( Elimination ) CH3 – CH – CH – CH3 Br Br

(iii) Systemic Change in hybridization of (C2- C3): CH3 – CH – CH – CH3 OH OH (Sp3) 2 3 Sp2 Sp3 CH3 – CH = CH – CH3 (Sp2) 2 3 (SP SP2) Conservation of hybridization Br Br Sp3 Sp CH3 – C  C – CH3 (Sp) 2 3

iv ) Systemic Change in the stereoisomerism:   CH3 – CH – CH – CH3 OH OH Optical Change CH3 – CH = CH – CH3 Geometrical Conservation Of Chirality Br Br Loss of CH3 C  C – CH3 No Stereo Isomers Geo. Opt. Creation of Geo. Chirality

(V) Systemic Change in the IR bands: CH3 – CH – CH – CH3 OH OH (  OH ) CH3 – CH = CH – CH3 ( C = C ) Br Br ( C– Br ) CH3 – CH  CH– CH3 ( C  C )

vi) Systemic Change in the 1HNMR: CH3 – CH – CH – CH3 OH OH CH3 –CH = CH – CH3 Br Br CH3 – C  C– CH3 Appearance Of (CH – o-, and OH signals) Appearance of olefin Proton signals Disappearance of OH Signals Disappearance Of (H – C – Br

SP- 2 Aromatic Compound C7H8 reacts with Cr2O3 / acetic acid to give C7 H6 O (B) which reacts with K MnO4 / Conc. H2SO4 to give C7 H6 O2 (C). By Heating (C) with Soda lime under dry Conditions gives liquid (E). Write the names and draw the structural formulas of Compounds (A - D) 2) Give the systemic clockwise Chemical relations between Compounds in a systemic diagram. (A D)

3) Monitor the Changes of the following items in the systemic: i) Functional groups. ii) Type of reaction in each step. iii) I. R spectra. iv) 1H. N. M. R. Spectra. v) Molecular ion peaks in the Mass spectra. vi) Ease of reactions with Electrophiles. CH3 Toluene - A CHO Benzaldehyde- B (A) 1) COOH Benzoic acid -C Benzene - D

2) 3.i CHO CH3 Cr2O3/ Acetic acid COOH Soda lime / heat CH3 Cl3/ AlCl3 KMnO4 / H2 SO4 2) Methyl G. Formyl G Phenyl Carboxy 3.i

of γ c=o γ OH carboxyl.acidband 3.ii) A B D C Oxidation Decarboxylation F.C. Alkylation 3.iii) Systemic Change in the IR- Spectra. γ CH3 γ CH (ar.) (A) γ C=O(ald.) γ C-H (ar.) (B) Appearance of γ C = O ald. band of γ C=O , γ OH Carboxylic acid bands of γ CH3 band I-R Spetra γ C=O(acid.) γ OH (acid.) γ C-H (ar.) Dissappearance of γ c=o γ OH carboxyl.acidband

3. iv. Systemic Change in the HNMR: S. (3H, C H3 m.(5H, C6H5) S. (H, C HO) m.( 5H, C6H5) Appearance of CHO Signal Dissappearance of CH Aldehydic & Appearance 1H. N. M. R of (3H, CH3) Appearance of COOH proton signals. m. (5H, C6H5) Appearance S. (H, COOH) m.( 5H, C6H5) of COOH proton Signal

3. v. Systemic Change in Mass Spectra: m. u. M+.(A) , m/z =92 M+(.B) , m/z=106 (+ 14) m.u. M+.(D) m/z = 78 M+-( C), m/z=122 (-44) MS +16 (m.u) +14 (mu) (mu = Mass Unites) C6 H5 CH3 C6 H5 CHO Decreases C6 H6 C6 H5 COOH Ease of E.S. Increases 3.vi

Heterocyclic Compound (A) exist in liquid state SP3 Heterocyclic Compound (A) exist in liquid state Contains (S) reacts with CH2O / HCl to give ( C5H5 SCl) (B).Compound (B) reacts with (CH2)6 (NH4)4 in alco. to give (C5H4OS) (C) which reacts with KMnO4/Sulphuric acid to give (C5H5 O2S) (D) .Heating of (D) with Cu / in quinoline gives (A). Writ the names , and draw the structural formulas of compounds (A D). 2) Give the Systemic Clockwise Chemical relations between Compounds ( A D) in a Systemic diagram . 3) Monitor the Changes of the following items in this Systemic diagram. i) Type of reaction. ii) Ease of Nitration. iii) Systemic Change in the IR spectra when we move from compound (A to B – C – D ). iv) Systemic Change in 13CNMR when we move from compound ( (A to B – C – D) v) Systemic Change in the 1HNMR. signals , when we move from Compound ( A to B – C- D )

s s s (C) 2) HCl CH2Cl ( CH2)6 (NH2)4 / alco. Cu/ Quinaline KMnO4 COOH (Thiophene) (C) (Formyl thiophene) CHO (B) s CH2Cl ( 2- Chloromethyl thiophene) (D) ( 2- Carboxy thiophene) Cu/ Quinaline s ( CH2)6 (NH2)4 / alco. CH2O/ HCl CH2Cl CHO COOH KMnO4 Conc. H2 SO4 2)

c s 3.i) Type of reaction in each step : A B D (Substitution) (Oxid) (Chloromethylation ) (Substitution) (Oxid) (Elimination) ( Decarboxylation) 3. ii. Ease of Electrophelic substitution: CH2Cl s C-O-H o (Increases) ( Dicreases)

s 3. iii.I.R of CH2 C= C (Disappearance ) Appeases of CH2Cl s COOH CHO (Disappearance ) of CH, γ CO acid Appearance Appeases of γ C =O ald. of CH2 C= C γ CH2 of γ C =O, OH acid  C = O (ald.)  C= C  C = O, γ (ald) (aciad)  C=C

s 3.v. MS: 3. iv. 1HNMR: C H2Cl of H-C =O singlet M+ (A) 84 M+ (B) COOH Appearance of CH2 singlet of H-C =O singlet Disappearance COOH singlet CHO of COOH Signal 3.v. MS: M+ (A) 84 M+ (B) 132 / 134 M+ (D) 128 M+(C) 113 + 48/50 mu -19/ 21 - 45 m u + 16

s 3.vi. 13CNMR C-Cl signal Disappearance of Appearance of COOH Signal. (t) s CH2Cl S\ OH O Appearance of C - Cl Signal Disappearance of COOH Signal. d- H C of COOH C-Cl signal Appearance of C = O Signal

( SP4) ( SP-2) ( SPO) SYSTEMIC PROBLEM SOLVING METHODOLOGY SP-F) P1 P3 ? √ ? Stage (2) Stage (1) P1 P3 P2 P4 SP ? ? ? √ P1 P3 P2 P4 SP ( SP4) ? ? ? √ ( SP-2) ? ? Stage ( SPO) (3) P1 P3 P2 P4 SP √ ? Stage (4) (SP3) SYSTEMIC PROBLEM SOLVING METHODOLOGY P1 P3 P2 P4 SP √ SP-F)

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.

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),859-863 [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), 1078. 3-. 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, 12-17 August 2006]. 5- Hollingworth , R, Chemical Education Journal (CEJ),2001,.5(.2 ), http://www.juen.ac.jp/scien/cssj/cejrnlE.html