1. SYSTEMIC PROBLEM SOLVING TO ASSESS STUDENT ACHEVEMENTS IN CHEMTSTRYBY
&
* 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 78712
Website:
42 nd IUPAC Congress, Glasgow, Aug 2- 7 (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. 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

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

7. 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

8. 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)

9. 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).

10. 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

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

12. dil . alk. CH3 - CH – CH- CH3 heat
3) CH3 - C = C - CH3 (A)
(SP2)
CH3 - C  C - CH3 (D)
(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

13. (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

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

15. 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

16. (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 )

17. 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

18. 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)

19. 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

20. 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

21. 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

22. 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

23. 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

24. 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 )

25. 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)

26. 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)

27. 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

28. 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

29. 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

30. ( 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)

31. 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.

32. 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), 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, August 2006].
5- Hollingworth , R, Chemical Education Journal (CEJ),2001,.5(.2 ),