The Systemic Approach to Teaching and Learning Heterocyclic Chemistry

[SATLHC]:Operational Steps for Building Teaching

Units in Heterocyclic Chemistry

Feb.2013

A. F. M. Fahmy, J.J.Lagowski*Faculty of Science, Department of Chemistry

Ain Shams University, Abbassia, Cairo, EGYPTE-mail:afmfahmy42@gmail.com

*University of Texas at Austin ,USAWebsite:satlcentral.com

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

#

Introduction # SATL-Teaching Strategy.

#Difficulties in Learning Heterocyclic Chemistry.

# SATL-in Building Unites [General strategy].# Scienario of Building unite on 5-

Membered Heterocycles.[Pyrrole – Furan – Thiophene]

#Conclusions.

INTRODUCTION:

-After the wide spread of the systematization in various activities including, tourism, economy, security, education,…etc ,

and after globalization became a reality that we live .

-SATL became a must and Chemical Education Reform (CER)has gained 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.

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.

Pungente, and Badger 2003 stated that the primary goal of teaching introductory organic chemistry is to take students beyond the simple cognitive levels of knowledge and comprehension using synthesis and analysis – rather than rote memory.

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).

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 chemistry, as well as other subjects.

SATL, will help students to understand interrelationships between concepts in a greater context.

SATL Helps teachers to teach and learners to learn.

What is the SATL?

- We mean an arrangement of concepts or issues through interacting systems in which all relationships between concepts and issues are made, clear up front, to the teacher and learner.

Fig: 1aLA

concept concept concept concept concept concept concept concept

Fig: 1bSA

concept concept

concept concept

concept concept

concept concept

Systemic teaching strategy:[STS]

- we started teaching 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.

SD

0SD

f

SD

2

SD

1

Fig (2): Systemic teaching strategy

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 University Level.

The systemic diagrams involved in teaching are similar except that the number of known relationships

( )and the unknown )?)ones as indicated in the Fig.2.

-In this presentation, various examples of systemic heterocyclic teaching materials will be illustrated.

Second: The Prerequisites needed for teaching the unite from previous studies (facts, concepts, laws, reaction types and skills) should be tabulated into a list.

.

Uses of SATL-in Building Unites:

[ General Building Strategy ] In SATL building strategy of unites , we convert the linearly based unites in chemistry to systemically - based

unites according to the following building strategy;

First: The systemic aims and the operational objectives for the unit should be defined in the frame of

national standards..

Third: Then content analysis of the linearly-based unite into facts, concepts, laws, reaction types, mental, and experimental skills.

Fourth: Draw a diagram illustrating linear relations among the concepts of the unite [Fig.3].  

.

HH

XX

EE

ZZ

YY

FF

GG

Fifth: We put the sign () on the already known relationships from previous studies. Then the remaining linear relations are unknown and signed by (?). So, the diagram in Fig-3 should be modified as shown in Fig. 4:

 

HH

XX

EE

ZZ

YY

FF

GG 1

2

34

5

6

?

??

Fig4: Showing linear relations between concepts after defining the known from the unknown ones.

Sixth: The diagram Fig.4 is modified to a systemic diagram SD0 Fig.5 by adding unknown relations between the concepts from (7-12).SD0 is known as the starting point of teaching the unite. 

.

Fig5: Showing systemic relations between concepts after defining the known from the unknown ones.

1

2

34

5

6

?

? ?

H

X

E

Z

Y

F

G

12 7

8

9

11

10

? ?

?

??

?

)SDss0)

 

Seventh: In the scenario for teaching

the unit the student study the relations (7, 8, and 9).So, he will be able to add

them to SD0 diagram to give SD1 diagram.Fig.6.

 

1

2

34

5

6

?

? ?

H

E

Z

Y

F

G

12 7

8

9

11

10

?

?

? X

Fig.6.[SD1]

At this stage of teaching the unite we can ask the students to build systemics showing the relations between the concepts (X, Y, Z, and E) via systemic assessment..

 

 

Fig.7.[SD2]

Eighth: In the next stage of the of the scenario

of teaching the unite, the student study the relations

(4, 5, 10, and 11) and then he will be able to add them

to SD1 to obtain SD2- Fig.7.1

2

34

5

6

?

H

E

Z

Y

F

G

12 7

8

9

11

10

?

X

 

 

Fig.8.[SD3]

1

2

34

5

6

H

E

Z

Y

F

G

12 7

8

9

11

10

X

Ninth: In the last stage of teaching the unit , the student studied the two relations (6, 12). Then adds them to SD2 to obtain SD3-Fig.8 where we reached to the end of the systemic teaching of the unite.

SD3 can be denoted as the terminal systemic SDf of teaching the unite .

 

.

Tenth: The scenario of teaching any course systemically - involves the development of a systemic diagram (SD0) that has determined the starting point of the course; it incorporates the prerequisite materials. The course ends with a terminal systemic (SDf) in which all the relationships between concepts are known (Fig. 8).

From SDO through SDf we crossover several systemics with known and unknown relationships (SD1, SD2, etc.).

 

Difficulties in Learning Heterocyclic Chemistry

By Traditional Methods The students find the following

difficulties in learning HC:

i) To Remember the structural formulas of

heterocycles and

chemical properties related to these

structures.

ii) To understand the systemic effect of

heteroatom on the

reactivity of both heterocycles and their

substituent's.

iii) To synthesize systemic chemical relations

between

compounds of the same or different

heterocycles.

iv) To understand the importance of

heterocycles in their life's.

v) To Design synthesis of new target

heterocycles via RSA.

vi) To connect between different heterocyclic

systems.

SATLHC

Pure Applied

- Synthesis- E-Substitution- Nu-Substitution- Addition- Cycloaddaition- Ring Opening- Het. Int. Conversion

- Pharmaceuticals- Food Additives- Plant growth regulators- Insecticides- Herbicides- Corrosion Inhibitors- Super conductors.- Dyes

- Photographic materials etc..)

[LATLHC]

Z

Het.

X

Z

Het. Y

Z

Het.

E

Z

Het.F X,Y,E,F

[SATLHC]

Z = N, O, S

)Functional Groups)

Z

Het.

Uses of SATL-in Building Unites

In Heterocyclic Chemistry: A course of heterocyclic

chemistry using the SATL

technique was organized and

taught to the 3rd year students at

Ain Shams University.

SATLHC means survey study on

the reactivity of both heterocycles

and substituent's and the effect of

heteroatom on their possible

chemical relations.

C-Heteroatom: [)Z) = NH, O, S]

D-Substituents:[)G) = R, - CH2 - X, - X, -CH2 - OH - NH2, - CHO, - COR, - COOH]

GA-Reactivity of the Nucleus

B-Reactivity of the Substituents

Z

SATL-HC

Z

Scienario of Building unite on 5-Membered Heterocycles

First: Draw a diagram summarizes linear comparative reactivites of the five membered heterocycles as model of heterocyclic compounds, and their possible chemical relations. [Fig.1]  

Z CHO

ZRZ CO2H

Z

Z

O

OZ

O

Z N2Ph

Z NO2

ZBr

Z SO3H

Z COCH3

DMF/ POCl3

Z = NH, O (heat)Z = S (Cu/quinoline)

anhydride(Z = O,S)

Maletic

red. (Z = O, NH)

Z = NH, (RMgX)(Z = O,S) alkene/

H3PO4

Z = NH,

i) CH3CONR2/POCl3

ii) aq Na OAc

Z = NH (NBS)Z = O Br2/dioxanZ = S Br2/ AcOH

Z = NH, O, C6H5N-SO3

Z = S H2SO4

Z = NH, O, SAcONO2/

Ac2O

PhN2

Z = NH

+

Z CH2OH

HCHO/base(Z = NH)

Z = NH, O, S [Fig.1]

The diagram Fig.1 represents the comparative reactivates of five membered heterocyclic rings, and gives the linear separated chemical relations between (Pyrrole,Furan,Thiophene), and their compounds.

Second:- The diagram Fig.1 is modified to a

systemic diagram SD1 Fig.2 by adding relations between

Heterocyclic derivatives.

- SD1 summarizes the comparative reactivates of both heterocyclic nucleus and substituent's.

Z CHO

ZRZ CO2H

Z

Z

O

OZ

O

Z N2Ph

Z NO2

ZBr

Z SO3H

Z COCH3

Oxidation

Wolff/Kishener

reducation

DMF/ POCl3

Z = NH, O (heat)Z = S (Cu/quinoline)

anhydride(Z = O,S)

Maletic

red. (Z = O, NH)

Z = NH, (RMgX)(Z = O,S) alkene/

HPO4

Z = NH,

i) CH3CONR2/POCl3ii) aq Na OAc

Z = NH (NBS)Z = O Br2/dioxanZ = S Br2/ AcOH

Z = NH, O, C6H5N-SO3

Z = S H2SO4

Z = NH, O, SAcONO2/

Ac2O

PhN2Z = NH

+

(4)

(5)

(6)

(7)SD 1

?

??

?

Z CH2OH

HCHO/base(Z = NH)

(3)?

?

(1)

?

(2)

Fig.2

The systemic diagram SD1 shows

unknown chemical relations (1-7)

between heterocyclic compounds.

These relations will be clarified

later during the study of the unite

[ pyrrole, furan and thiophen ].

At this stage of teaching the

unite we can ask the Students to

answer the following Systemic

Assessmet-1.

ASSESSMENT – I

ON SD1

ASSESSMENT – I

ON SD1QI) Draw systemic diagrams

illustrating the chemical relations between compounds in each of the following sets. [SSnQ,s]

Z CHO Z COOHZ

1) ,, (Clockwise)

Z CHO Z COOHZ

2) ,,

Z R

,

A I - 1

Z COOH Z CHO

Z

OxidK2Cr2O7 / H2SO4

i)DMF, POCl3

ii)AcONaZ= O,NH heat 200oCZ =S Cu/Quinoline

QII) Complete the following systemic diagrams:

Z

)Z = NH)

....................

.......... ..........

1)

Z

..........

..........

..........

CHO

i) DMF /POCl3

ii)aq. Na2CO3

CH3MgX

)Z = .......)

2)

A II - 2

Z Z CH3

Z CHOi) DMF/ POCl3

ii) Na2CO3

Wolf-Kishner reduction

CH3MgX

)Z = NH)

Reactions of pyrrole, furan, thiophene and their compounds

Reactions of pyrrole, furan, thiophene and their compoundsI-Pyrrole:

(Prerequisites SD1)I-Pyrrole:

(Prerequisites SD1) Third: From Fig.1 the student can deduce the reactions of pyrrole as in

the following diagram (Fig. 3).

NH

HN

i) DMF/POCl3

ii) aq. Na2CO3

HN

HN

Ac2O-10C

AcONO2PhN2

THFNBS

red.

(NH4)2CO3130cSealed Vessel

CO2NH4

+ -

+ -

BrHN

N2 PhHN

NO2

HN

HN

ii)HCl

NaOH

RMgX

i) C6H5NSO3

i) RCONR2

ii) NaOAc

COR

SO3HHN

RHN

CH2OHHN

Cl

N

CHO

H2/Rany Ni

N

CH2Cl2

CH3Li /

+

CHCl3/baseHCHO

)Fig. 3.(

The diagram (Fig. 3) represents

the reactivity of (pyrrole

nucleus), and gives the linear

separated chemical relations

between pyrrole and its

compounds.

Fourth: We can illustrate the

chemical relations in

(Fig.3) systemically by

modification of SD1 to SD2

(Fig.4) )Z = NH):

HN

HN

N

HN

HN

HN

N

H

HN

R=CH3

(1)

(3)CHO

Cl

?

?

ReductionOxid.

R=CH3base

HCHO

130ocbaseCHCl3/

i)DMF/POCl3

ii) aq.Na2CO3

RMgX

(2)(4)

(5)

Ac2O,-10oc

AcONO2

+PhN2

N2Ph

heat

200oC

(8)

?

?

?

?

R

CH2OH

NO2

Br

SO3H

COR`

i) R`CONR2/POCl3

ii) NaOAc

i) C6H5NSO3

ii) HCl

?

H

?

HN

NH

CO2NH4

CH2Cl2/

CH3Li

(NH4)2CO3

N COOH

NBS/THF

(6)

(7)

+ -

N

N

Wolff/ Kishner

red.

SD 2SD 2

Systemic diagram (SD2) shows; (i) known chemical relations between pyrrole and its compounds (ii) unknown chemical relations between pyrrole compounds (1-8),

should be clarified during the study of pyrrole compounds.

)Fig.4(

Fifth : After Study of pyrrole compounds [G = R, CH2OH, CHO, RCO,

COOH , NH2):

HN

HN

HN

HN

NH

HN

CHOCl

Oxid

CH2O/NaOH

baseCHCl3/

AlkylationRMgx

Wolff-kishner

red.

Nitration

Ac2O-10C

AcONO2

+PhN2

R = CH3

Oxid., chromic acid

heat200c

CH2OH

rearang.Curtius

redNO2

SO3H

i) R`CONR2/POCl3

ii) aq. Na2CO3i) C6H5NSO3

ii) HCl

aq. alkaline KMnO4

i) DMF/poCl3;

ii) aq Na2 CO3

HN

HN

(NH4)2CO3

hydroCO2NH4

NH

COR`

HN CHBr2

DiboraneR=CH3 NBS,CHCl3

refulx

R=CH3

(R= CH3) hydrolysis

H2/PdR= CH3

NaBH4

HN

HN

HN

Ag2CO3/CeliteLTA/AcOH,

PhN2

CO2H

N2Ph NBS/THF

CON3

HN

pyridneSOCl2/

NaN3

COClNNH2

HNH

bromination Br

CH2Cl2 / CH3Li

150-200C

NN

H2-Rany Ni

R

KMnO4

Vap.

Phase

decarbonylation

SD 3SD 3

+

The student can modify (SD 2 to SD 3) Fig.5 by adding chemical relations (1 – 8).

Fig.5

At this stage of teaching the unite we can

ask the Students to answer the following

Systemic Assessmet-2.

ASSESSMENT – IION SD3

ASSESSMENT – IION SD3

QI) Draw systemic diagrams illustrating the chemical relations between compounds of each of the following sets:[ SSnQ,s] )clockwise)

NH

NNH

COOH CHO

,,1-

H

NH

,,,NO2

NH

COOH NH

CHONH

2-

H H HH

N

,,,N N N2PhNCOONH4 COOH

3-

A I - 1

NH

NH

CHO

NH

COOH

aq. alk.200oC

heatKMnO4

i)DMF, POCl3

ii) aq. Na2 CO3

QII)

A) a: ))

The systemic diagram represents the correct chemical relations between pyrrole

and its related compounds is one of the following:

[SMCQ,s]NH

NH

COOH NH

CHO

NH CHO

NH

NH

CH3

NH

NH

CH2OH NH

CHO

NH CO2H

NH NO2

NH

a)

i) DMF/ POCl3ii) aq. Na2CO3

(......................)

b)

(......................)

c)

(......................)

d)

(......................)

Vap. Phase

i) DMF/ POCl3ii) aq. Na2CO3

i) CH3MgBrii) hydro.

H2/Pd

i) DMF/ POCl3ii) aq. Na2CO3

aq. alk.KMnO4

heat 200oC

Nitration

Conc. HNO3H3SO4

heat 200oC

NaBH4

QIII) Which of the following systemics are true and which are false:

[STFQ,s]NH

NH

COOH NH

CHO

( )

i) DMF/ POCl3

ii) aq. Na2CO3

heat 100oC

aq. alk.KMnO4

NH

CHO

NH N

HCH3

( )

i) DMF/ POCl3

ii) aq. Na2CO3

Wolff.kishner

red

i) CH3 MgBrii) hydro.

a) b)

A) a: )x); b: )) c: )x); d: ))

NH CO2H

NH

N2Ph NH

( )

heat 100oC

NH

CHO

NH

NH

CH2OH

( )

i) DMF/ POCl3

ii) aq. Na2CO3

i) CH2O/ii) NaOH

NaBH4

PhN2

+

PhN2

+

d)c)

QIV) Choose heterocyclic compounds from

column (A) and reaction conditions from column (B) to build the systemic diagram in column (C):

[SMQ,s]

)A))C))B)

DMF/POCl3

Aq. Na2CO3

H2/Pd

Alk. KMnO4

Heat 200oC

NH

NH

CHO

NH

COOH

NH

CH3

QV) Rearrange the compounds in the following SD to give correct chemical relations:[ SRQ,s]

NH

COOH NH

NH

NBS/THF

COONH4 NH

Brhydrolysis

)NH4)2 CO3/130C

Seald vesselBr2

200Cheat

A)

NH

COOH

NH

NH

NBS/THF

COONH4

NH

Br

hydrolysis

)NH4)2 CO3/130C

Seald vesselBr2

200Cheat

II-Furan: Prerequisite SD1

II-Furan: Prerequisite SD1Sixth: From Fig.1 the student can

deduce all the reactions

of furan [Z=O] as in Fig.6.

O

OO

O

O

O

O NO2

O Br

O Li

N

O CH3

O Et

CHO

O

N O

COOEt

i) DMF, POCl3

ii) aq Na2 CO3Maleic anhydride

2,3-Pyridyne

130C

N3COOEt

CH2N2/ hv

ii) pyridine

i) AcONO2

O SO3H

Br2/dioxan

-5Cii) HCl

i)C6H5N.SO3

O COR`

ii) aq. Na2CO3

ZnCl2 /175C

(CH3)2 C=CH2

i) R`CONR2/POCl3

O B ut

EtI

CH3I

Bun Li

O

OOH H

H2/CatH/H2O+

The above diagram represents the reactivity of furan nucleus, and gives the linear separated chemical relations between furan and its compounds.

Fig.6

Seventh: From SD1 the student can illustrate the systemic chemical

relations in (Fig. 7) by modifying (SD1 to SD4) [Z=O]

The Systemic diagram SD4 shows; (i) known chemical relation between furan and its compounds (ii) unknown chemical relations between furan compounds. (1-7)

SD 4SD 4?

O

O

O

O

O

O

O NO2

O4

Br

?

?

O Li

O CH3

O CH2CH3

CHO

O

N O

COOEt

i) DMF, POCl3

ii) aq Na2 CO3

Malic anhydride

(2,3)Pyridyne

130C

N3COOEt

CH2N2/hv

ii) pyridine

Heat (200C)

i) AcONO2

O SO3H

Br2/dioxan

-5C i) C6H5NSO3

ii) HCl

O

ZnCl2 /175C

(CH3)2 C=CH2

Ac2O, SnCl4

O But

EtI

CH3I

Bun Li

O

OOH HH2/Cat

H/H2O

O CO2H

6

?

?

2

7

5

3

1

?

?

Oxidation Reduction

+

COCH3

N

O CH2OH

Fig. 7

Eighth: After the next stage of the study of furan compounds [G = R, X, CH2OH, CHO, RCO, COOH] the student can modify (SD4 to SD5) Fig.8 by additions chemical relations (1-7).

In the systemic diagram (SD5) the chemical relations between furan compounds are clarified.

- At this stage of teaching the unite we can ask the Students to answer the following

Systemic Assessmet-3

SD5SD5

O

O

O

O

O

O NO2

O LiO CH3

O CH2CH3

CHO

O

N O

CO2Et

2,3 pyridyne

130C

CH2N2

ii) pyridine

Heat (200C)

i) AcONO2

Br2/dioxan

H2SO4

H2SO4

0Ci)C6H5N.SO3

ii) HCl O COCH3

ZnCl2 /175C

(CH3)2 C=CH2

Ac2O, SnCl4

O But

EtI

CH3I

Bun Li

O

OOH H

H2/Cat

H /H2O

O CO2H

Red.wolff Kishner

250C red.

Cu-Cr2O3/ -C

N3COOEt

O MgBr

HNO3

ii)hydro

i)CO2

Mg/cuether

COOHBr

O

red

NaBH4

H2 / Ni-Co

CH2OH

K2Or2 O7/dil H2SO4

Oxid

N

+

O

Br2

heatCu-Quinoline

O O SO3HBr

Maleic anhydride

i) DMF/ POCl3

ii) Na2CO3

O

Fig.8

ASSESSMENT – IIION SD5

ASSESSMENT – IIION SD5

QI) Draw systemic diagrams illustrating the possible chemical relations between compounds of each of following sets:[SSyQ,s]

O , ,, O EtOOLi CCH3

O3-

O ,, OO COOHCHO

2-

O , ,, O CO2HOO Br COOHBr

1-

A I – 1

O O

Br2

Cu/quinoline

heat200oc

COOH

Br2 / dioxan

-5oCOO Br

BrCOOH

QII) Which of the following systemics are true and which are false:

[STFQs]O

O Br O SO3H

a) ( )

i) C6H5NSO3

ii) HCl

Br2/ dioxan -5oC

H2SO4

O CO2H

O NO2 O

b) ( )

i) AcONO2

ii) Pyridine heat200oC

HNO3

O COCH3

OO CH2

CH3

c ( ) d) ( )

Ac2O,SnCl4

i) BunLiii) CH3CH2I

Wolffkishner

red.

O CH3

O CHO O CH2OH

K2Cr2O7/H2SO4

NaBH4

H2/Ni-CO

A ) a: )); b: )x) c: )); d: )x)

List (I) List (II)

1)

2)

3)

1)

2)

O CH3

H2/Ni-Co

O CH2OH

NaBH4

O CHOi) DMF, POCl3

ii) aq. Na2 CO3O

i) BunLiii) CH3I

Cu-Cr2O3/C250oC

O CH3

H2/Ni-Co

O CH2OH

NaBH4

O CHOi) DMF, POCl3

ii) aq. Na2 CO3O

i) BunLiii) CH3I

Cu-Cr2O3/C250oC

O CH3

O CHOO

i) DMF, POCl3

ii) aq. Na2 CO3

Cu-Cr2O3/C250oC

i) BunLiii) CH3I

O CH3

O CH2OHO CHO

O CH3

O CHOO

i) DMF, POCl3

ii) aq. Na2 CO3

Cu-Cr2O3/C250oC

H2/Ni-Co

NaBH4

H2/Ni-Co

Cu-Cr2O3/C250oC

QIII: Link systemics from list )I) to one systemic in list )II):

[SMQ,s]

III-Thiophene: (Prerequisite SD1)

III-Thiophene: (Prerequisite SD1)Ninth: From Fig.1 the student can

summarize all the reactions of thiophene in the following

diagram (Fig. 9). [Z=S]

The above diagram represents the reactivity of (thiophene nucleus), and gives the linear separated chemical relations between thiophene, and thiophene compounds.

290C, 21 atm.

CH3COCl/SnCl4

C6 H6 , 0oC

NO2BF4

CH3CH = CH2S

S

S

SS

CH3CH3

CH3CH3

S

O

O

O

i) DMF, POCl3

ii) aq. NaOAcLi/NH3, CH3OH

S

S SO3H S COCH3

S Pri

S

ii)I2

i)(CH3)3B

i)Et3BLiii)I2

S CH3

S Et

SCH2O/HCl

CH2Cl

Bun Li

CHO

NO2

Br

Br2/AcOH

ether

Benzyne

C6H5NSO3

S/700oC

Rany NiMaleic anhydride

Tenth: The student can illustrate the chemical relations in (Fig. 10) systemically by modifying (SD1 to SD6) [Z = S ]

SD6SD6

S

S290C, 21 atm.

CH3COCl/SnCl4

C6 H6 ,

NO2BF4

CH3 CH=CH2

S

S

SS+

red

S

O

O

O

i) DMF, POCl3

ii) aq. NaOAc

Li/NH3, CH3OH

Maleicahydride

S

S SO3H

S NO2

S Pri

S ii) I2

I) (CH3)3B2

i)Et3B

Li

ii)I2

S CH3

S Et

S

CH2O/HCl

CH2Cl

CHO

ether

Br2/AcOH

C6H5NSO3

Benzyne

S, 200

Cu / Quinoline

heatCO2H

?

?

?

(4)(6)

(5)

(3)

Br

COCH3

Bnu Li

? (2)

?(1)

reductionoxidation

Red.

The above systemic diagram (SD 6) shows; (i) The known chemical relations between thiophene and its compounds, (ii) The unknown chemical relations between thiophene compounds (1-6).

Fig. 10

Eleventh: After the next stage of the study of thiophene compounds [ G = R, X, CH2OH, CHO, RCO, COOH ] . The student can modify (SD6 to SD7) Fig.11 by addition of chemical relations (1-6).

In the (SD7) all chemical relations between thiophene compounds were clarified.

- At this stage of teaching the unite we can ask the Students to answer the following

Systemic Assessmet-4

SD 7SD 7 Fig.11

ASSESSMENT – IVON SD7

ASSESSMENT – IVON SD7

QI) Draw systemic diagrams illustrating the chemical relations between compounds of each of the following sets:[SSnQ,s]

S COOH S S CHO

1) , , (Clockwise)

S S Br S SO3H

2) , ,

S S COOH S COCH3

3) , ,

SS COOH S CHO

4) , , ,

S CH2Cl

A I – 1

S COOH

S

S CHO

K2Cr2O7/ H2SO4

Cu-Quinoline ii) NaoAc

i) DMF POCl3

QII) Complete the following systemic diagram:

O CH3

..........

..........

..........

....................

O

i) ...........ii) ..........

CH2OH

O CHO

)1)

)5)

)2))4)

)3)

A

O CH3 O

H2/ Ni-Co

)1)

)5))2))4) Cu- Cr2O3 /C

NaBH4

250oC

)3)

ii) CH3I

CH2OH

i) DMF, POCl3

ii) aq. Na2CO3 O CHOO

i) BunLi

SUMMARY: In the linear classical approach we

teach heterocycles as separate chemical reactions of the rings , also the relationships between heterocyclic derivatives are ambiguous infront of our students; however in SATL-HE the students are able to do the the following chemical transformations:

1- Heterocycles to another heterocycles in a direct pathway:

Het. AnotherHet.

Z Z

O SThiourea

O S

SH2

RNH2/

hvN

R

CH2Cl2/

baseNH

N

N

2,3-Pyridyne

O

aq N2H4

130oCNH

NN

N

Examples:

S

2- Three-membered to four-membered heterocycles via

aliphatic compounds and vis versa:Aliphatic

Compound

Z

Z

To ToO

O

Ph3P H2CO/

H+e.g:

Aliphatic Compound

Z

ZX

ToTo

To

O

NH

O

NR

Ph CO3H

RN3,

e.g:

3- Heterocyclic derivative to another hetercyclic derivative:X

G

X

YHet. Het.

Example:

Z Br

H2SO4

Z SO3H

H2SO4

Z COCH3

)Z = O, S)

4- Aliphatic compound to another aliphatic compound

via heterocycle:Aliphatic

compoundAliphatic

compoundToTo

X

OH Cl

OHO

NH3

OH NH2

SR

S S R

Red.ii) BR3

i) Bun-Li

RanyNi

5- Heterocycles to homocycles:X

Het. HO

S

Benzynee.g.

O

O

CH3CH3

OH

OHCH3

KOH

O O R

RR RC C

R = (Si (CH3)3)

6- Design synthesis of any target heterocyclic system via

Retro-Synthesitic Analysis[RSA]: Synthesis of [IMIDES]

R.S.A. Decomposition

Synthesis

N

O

O

Ar

N

O

O

Ar

: Al Cl3

+

O Al Cl3

N

O

Ar

+

O

N

O

Ar

Al Cl3/

O Al Cl3

N

O

Ar

+

N

O

O

Ar

Al Cl3

+

ClH

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.

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), 1078.

)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., Lagowski, J.J.; Systemic Approach in Teaching and Learning Aliphatic Chemistry; Modern Arab Establishment for printing, publishing; Cairo, Egypt )2000).

)5) Fahmy A. F. M., El-Hashash M., Systemic Approach in Teaching and Learning Heterocyclic Chemistry. Science Education Center, Cairo, Egypt )1999).

)6) 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).

(7 )Systemic assessment as a new tool for assessing students learning In Chemistryusing SATL methods: Systemic true false [STFQs] and systemic sequencing [SSQs] question types. A.F.M. Fahmy and J. J. Lagowski

AJCE. 2, )2)66-78)2012).

THAK YOU FOR YOUR

ATTENTION