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The Systemic Approach to Teaching and Learning Heterocyclic Chemistry [SATLHC]: Operational Steps for Building Teaching Units in Heterocyclic Chemistry. A. F. M. Fahmy , J.J.Lagowski* Faculty of Science, Department of Chemistry

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The systemic approach to teaching and learning heterocyclic chemistry satlhc

The Systemic Approach to Teaching and Learning Heterocyclic Chemistry [SATLHC]:

Operational Steps for Building Teaching Units in Heterocyclic Chemistry

A. F. M. Fahmy, J.J.Lagowski*

Faculty of Science, Department of Chemistry

Ain Shams University, Abbassia, Cairo, EGYPTE-mail:[email protected]

*University of Texas at Austin ,USA

Website:satlcentral.com

Feb.2013


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • If their is no Teaching Chemistry their is no Chemistry

  • Good chemistry teaching

excellent chemistry research


The systemic approach to teaching and learning heterocyclic chemistry satlhc

# 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.


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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.


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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.


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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.


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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.


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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:1a

LA

concept

concept

concept

concept

concept

Fig:1b

SA

concept

concept

concept


The systemic approach to teaching and learning heterocyclic chemistry satlhc

SD1

SD2

SD0

SDf

  • 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.

Fig (2): Systemic teaching strategy


The systemic approach to teaching and learning heterocyclic chemistry satlhc

  • 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.

    • A list of SATLCmaterials were produced in Egypt

    • e.g.:SATLGeneral Chemistry for secondary schools. SATLAliphatic, Aromatic, Green chemistry and Heterocyclic Chemistry for University Level.

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    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..

    .

    Second: The Prerequisites needed for teaching the unite from previous studies (facts, concepts, laws, reaction types

    and skills) should be tabulated into a list.

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    H

    G

    Y

    X

    F

    Z

    E

    • Fourth: Draw a diagram illustrating linear relations

    • among the concepts of the unite [Fig.3].

    .


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    H

    6

    ?

    1

    G

    Y

    ?

    5

    X

    2

    ?

    F

    4

    3

    Z

    E

    • Fifth: We put the sign () on the already knownrelationships 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:

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    7

    H

    12

    ?

    ?

    G

    Y

    1

    6

    ?

    ?

    5

    ?

    ?

    11

    X

    8

    2

    ?

    F

    Z

    4

    3

    ?

    ?

    E

    10

    9

    (SDss0)

    • Sixth: The diagram Fig.4 is modified to a systemic

    • diagram SD0Fig.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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    7

    H

    12

    ?

    G

    Y

    1

    6

    ?

    ?

    5

    11

    X

    8

    ?

    2

    ?

    F

    Z

    4

    3

    ?

    E

    10

    9

    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.

    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..


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    7

    H

    12

    ?

    G

    Y

    ?

    1

    6

    5

    11

    X

    8

    2

    F

    Z

    4

    3

    E

    10

    9

    • 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.

    Fig.7.[SD2]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    7

    H

    12

    G

    Y

    6

    1

    5

    11

    X

    8

    2

    F

    Z

    4

    3

    E

    10

    9

    • Ninth: In the last stage of teaching the unit , the student studied the two relations (6, 12). Then adds them toSD2toobtainSD3-Fig.8where we reached to the end of the

    • systemic teaching of the unite.

    Fig.8.[SD3]

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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 SDfwe crossover several systemics

    • with known and unknown relationships (SD1, SD2, etc.).

    .


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    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) Tounderstand the systemic effect of heteroatom on the

    • reactivity of both heterocycles and their substituent's.

    • iii) Tosynthesize systemic chemical relations between

    • compounds of the same or different heterocycles.

    • iv) Tounderstand 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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    SATLHC

    Pure

    Applied

    - Synthesis

    - Pharmaceuticals

    - E-Substitution

    - Food Additives

    - Nu-Substitution

    - Plant growth regulators

    - Addition

    - Insecticides

    - Cycloaddaition

    - Herbicides

    - Ring Opening

    - Corrosion Inhibitors

    X

    - Het. Int. Conversion

    - Super conductors.

    - Dyes

    - Photographic materials

    Z

    etc..)

    Het.

    Z

    Z

    X,Y,E,F

    F

    Het.

    Y

    Het.

    (Functional Groups)

    Z

    Z = N, O, S

    Het.

    Z

    Het.

    E

    [LATLHC]

    [SATLHC]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    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.

    • SATLHCmeans survey study on the reactivity of both heterocycles and substituent's and the effect of heteroatom on their possible chemical relations.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    G

    Z

    B-Reactivity of

    A-Reactivity of

    the Substituents

    the Nucleus

    SATL-HC

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

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    [Fig.1]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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.1is modified to a systemic diagram SD1

    • Fig.2 by adding relations between Heterocyclic derivatives.

    • - SD1summarizes the comparative reactivates of both heterocyclic nucleus and substituent's.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Fig.2


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • The systemic diagram SD1shows 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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    ASSESSMENT – I

    ON SD1

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    A I - 1


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    QII) Complete the following systemic diagrams:

    A II - 2


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Cl

    CHO

    N

    N

    H

    N

    N

    CH3Li /

    i) DMF/POCl3

    ii) aq. Na2CO3

    H

    H2/Rany Ni

    CH2Cl2

    + -

    red.

    CO2NH4

    N

    CHCl3/base

    H

    CH2OH

    HCHO

    (NH4)2CO3

    N

    130c

    Sealed Vessel

    H

    NaOH

    RMgX

    NBS

    R

    THF

    N

    + -

    Br

    N

    N

    i) C6H5NSO3

    H

    H

    H

    ii)HCl

    +

    PhN2

    AcONO2

    Ac2O

    -10C

    i) RCONR2

    ii) NaOAc

    SO3H

    N

    N2 Ph

    N

    H

    H

    NO2

    N

    H

    COR

    N

    H

    Reactions of pyrrole, furan, thiophene and their compounds

    I-Pyrrole: (Prerequisites SD1)

    • Third:From Fig.1 the student can deduce the reactions of pyrrole as in

    • the following diagram(Fig. 3).

    (Fig. 3).


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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):


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Reduction

    Oxid.

    Wolff/ Kishner

    red.

    ?

    CHO

    N

    (3)

    H

    Cl

    N

    i)DMF/POCl3

    ii) aq.Na2CO3

    R=CH3

    CH2Cl2/

    CH2OH

    N

    N

    CO2NH4

    N

    H

    CH3Li

    H

    (8)

    HCHO

    ?

    (NH4)2CO3

    R=CH3

    CHCl3/

    base

    ?

    base

    (1)

    130oc

    RMgX

    heat

    COOH

    N

    R

    200oC

    N

    H

    i) R`CONR2/POCl3

    ii) NaOAc

    N

    +

    PhN2

    (4)

    (2)

    H

    ?

    ?

    + -

    i) C6H5NSO3

    ii) HCl

    (5)

    N

    N2Ph

    N

    COR`

    AcONO2

    ?

    H

    H

    Ac2O,-10oc

    N

    SO3H

    H

    NBS/THF

    ?

    N

    NO2

    (6)

    H

    Br

    N

    SD 2

    H

    ?

    (7)

    (Fig.4)

    • 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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    KMnO4

    R= CH3

    aq. alkaline KMnO4

    H2/Pd

    Oxid

    CHO

    N

    hydrolysis

    Cl

    Vap. Phase decarbonylation

    H

    (R= CH3)

    Ag2CO3/Celite

    N

    N

    LTA/AcOH, 

    NaBH4

    CH2Cl2 / CH3Li

    i) DMF/poCl3;

    ii)aq Na2 CO3

    CHBr2

    CHCl3/

    N

    N

    N

    base

    CH2OH

    H

    H

    H

    H2-Rany Ni

    CH2O/

    R=CH3

    R=CH3

    150-200C

    hydro

    NBS,CHCl3

    refulx

    NaOH

    N

    CO2NH4

    Diborane

    H

    (NH4)2CO3

    RMgx

    heat

    Alkylation

    200c

    R

    N

    N

    CO2H

    +

    H

    PhN2

    N

    H

    i) R`CONR2/POCl3

    ii) aq. Na2CO3

    +

    PhN2

    H

    Wolff-

    kishner

    red.

    N

    NBS/THF

    i) C6H5NSO3

    ii) HCl

    N2Ph

    H

    AcONO2

    bromination

    SOCl2/

    N

    Ac2O-10C

    COR`

    Br

    pyridne

    N

    N

    SO3H

    H

    H

    H

    Nitration

    COCl

    red

    N

    NO2

    N

    H

    H

    N

    NH2

    NaN3

    H

    Curtius

    N

    CON3

    rearang.

    SD 3

    H

    R = CH3

    Oxid., chromic acid

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

    • COOH , NH2):

    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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    1-

    ,

    ,

    N

    N

    N

    COOH

    CHO

    H

    H

    H

    2-

    ,

    ,

    ,

    N

    N

    N

    NO2

    COOH

    CHO

    N

    H

    H

    H

    H

    3-

    ,

    ,

    ,

    N

    N

    N

    COONH4

    N2Ph

    N

    COOH

    H

    H

    H

    H

    ASSESSMENT – II

    ON SD3

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

    (clockwise)


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    COOH

    N

    H

    aq. alk.

    heat

    200oC

    KMnO4

    i)DMF, POCl3

    ii) aq. Na2 CO3

    N

    N

    CHO

    H

    H

    A I - 1


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    QII)

    The systemic diagram represents the correct chemical relations between pyrrole and its related compounds is one of the following:

    [SMCQ,s]

    A) a: ()


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

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

    [STFQ,s]

    A) a: (x); b: ()c: (x); d: ()


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

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

    [SMQ,s]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    NBS/THF

    N

    Br

    N

    H

    H

    (NH4)2 CO3/

    130C

    Seald vessel

    heat

    Br2

    200C

    NBS/THF

    COOH

    N

    N

    H

    H

    hydrolysis

    (NH4)2 CO3/

    130C

    Seald vessel

    COONH4

    N

    COOH

    N

    heat

    Br2

    H

    H

    200C

    hydrolysis

    COONH4

    Br

    N

    N

    H

    H

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

    A)


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    O

    CHO

    O

    O

    O

    O

    O

    i) DMF, POCl3

    ii) aq Na2 CO3

    Maleic anhydride

    H

    O

    O

    H

    O

    H2/Cat

    +

    H/H2O

    CH3I

    CH2N2/ hv

    O

    CH3

    N3COOEt

    N

    O

    Bun Li

    O

    Li

    EtI

    130C

    COOEt

    O

    Et

    2,3-Pyridyne

    (CH3)2 C=CH2

    N

    ZnCl2 /175C

    t

    O

    B

    O

    u

    i) R`CONR2/POCl3

    i) AcONO2

    ii) aq. Na2CO3

    ii) pyridine

    Br2/dioxan

    i)C6H5N.SO3

    -5C

    ii) HCl

    O

    COR`

    O

    NO2

    O

    O

    Br

    SO3H

    II-Furan:Prerequisite SD1

    • Sixth: From Fig.1 the student can deduce allthe reactions

    • of furan [Z=O] as in Fig.6.

    Fig.6

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Oxidation

    3

    Reduction

    CHO

    O

    ?

    O

    O

    O

    i) DMF, POCl3

    ii) aq Na2 CO3

    O

    CH2OH

    O

    ?

    O

    O

    1

    CH2N2/hv

    H

    O

    O

    H

    Malic anhydride

    N

    O

    H2/Cat

    N3COOEt

    CH3I

    COOEt

    O

    CH3

    +

    130C

    H/H2O

    O

    Li

    EtI

    Bun Li

    (2,3)Pyridyne

    N

    O

    CH2CH3

    Heat (200C)

    (CH3)2 C=CH2

    ZnCl2 /175C

    CO2H

    O

    O

    But

    O

    i) AcONO2

    ?

    Ac2O, SnCl4

    5

    2

    ii) pyridine

    Br2/dioxan

    ?

    -5C

    O

    NO2

    i) C6H5NSO3

    ii) HCl

    ?

    COCH3

    6

    O

    7

    SD 4

    4

    ?

    Br

    O

    SO3H

    O

    ?

    • Seventh: From SD1 the student can illustrate the systemic chemical

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

    Fig. 7

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Cu-Cr2O3/ -C

    K2Or2 O7/dil H2SO4

    CHO

    O

    250C red.

    NaBH4

    O

    Oxid

    red

    O

    O

    i) DMF/ POCl3

    CH2OH

    O

    ii) Na2CO3

    O

    H

    O

    O

    H

    O

    H2 / Ni-Co

    CH2N2

    Maleic anhydride

    +

    H /H2O

    N

    O

    O

    CH3I

    N3COOEt

    CO2Et

    O

    CH3

    H2/Cat

    130C

    O

    Li

    EtI

    Bun Li

    2,3 pyridyne

    N

    O

    CH2CH3

    Heat (200C)

    (CH3)2 C=CH2

    ZnCl2 /175C

    CO2H

    O

    O

    But

    O

    HNO3

    i)CO2

    i) AcONO2

    Ac2O, SnCl4

    ii) pyridine

    wolff Kishner

    ii)hydro

    Red.

    Br2

    Br2/dioxan

    O

    NO2

    i)C6H5N.SO3

    ii) HCl

    O

    MgBr

    0C

    O

    COCH3

    COOH

    O

    Mg/cu

    ether

    H2SO4

    Br

    Cu-Quinoline

    heat

    SD5

    H2SO4

    SO3H

    O

    Br

    O

    • 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).

    Fig.8

    • 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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    Br2

    COOH

    Br

    COOH

    O

    O

    heat

    200oc

    Cu/quinoline

    D

    Br2 / dioxan

    -5oC

    Br

    O

    O

    1-

    2-

    3-

    ,

    ,

    ,

    Br

    COOH

    Br

    O

    O

    O

    O

    CO2H

    ,

    ,

    COOH

    CHO

    O

    O

    O

    O

    ,

    ,

    ,

    CCH3

    Li

    O

    O

    O

    O

    Et

    ASSESSMENT – III

    ON SD5

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

    A I – 1


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

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

    A )a: (); b: (x)c: (); d: (x)


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

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

    [SMQ,s]


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    CHO

    S

    S

    CH2Cl

    S

    S

    CH2O/HCl

    i) DMF, POCl3

    ii) aq. NaOAc

    CH3

    CH3

    Li/NH3, CH3OH

    i)(CH3)3B

    S/700oC

    S

    CH3

    ii)I2

    CH3

    Bun Li

    CH3

    Rany Ni

    i)Et3B

    S

    Li

    O

    Maleic anhydride

    ii)I2

    CH3CH = CH2

    S

    S

    Et

    O

    S

    Benzyne

    290C, 21 atm.

    O

    Br2/AcOH

    S

    Pri

    ether

    NO2BF4

    CH3COCl/SnCl4

    C6H5NSO3

    C6 H6 , 0oC

    Br

    S

    NO2

    S

    S

    S

    SO3H

    COCH3

    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.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    ?

    oxidation

    reduction

    (2)

    CHO

    S

    +

    i) DMF, POCl3

    ii) aq. NaOAc

    S

    S

    S

    CH2Cl

    red

    S, 200

    Li/NH3,

    CH3OH

    CH2O/HCl

    O

    Red.

    I) (CH3)3B2

    O

    S

    ii) I2

    S

    CH3

    Maleic

    S

    Li

    Bnu Li

    ahydride

    i)Et3B

    O

    ii)I2

    Benzyne

    S

    Et

    CH3 CH=CH2

    Cu / Quinoline

    290C, 21 atm.

    heat

    CO2H

    S

    Pri

    S

    S

    (3)

    Br2/AcOH

    ?

    ether

    NO2BF4

    (1)

    C6H5NSO3

    CH3COCl/SnCl4

    Br

    S

    ?

    C6 H6 ,

    (5)

    S

    NO2

    ?

    S

    SO3H

    (4)

    ?

    (6)

    COCH3

    SD6

    S

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

    Fig. 10

    • 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).


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • Eleventh:Afterthe 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).

    SD 7

    Fig.11

    • 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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    ASSESSMENT – IV

    ON SD7

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    A I – 1


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    (1)

    ..........

    CH3

    CH2OH

    O

    O

    (5)

    (4)

    (2)

    ..........

    i) ...........

    ii) ..........

    ..........

    (3)

    ..........

    ..........

    CHO

    O

    (1)

    H2/ Ni-Co

    D

    CH2OH

    CH3

    O

    O

    (5)

    (4)

    Cu- Cr2O3 /C

    (2)

    i) BunLi

    NaBH4

    250oC

    ii) CH3I

    (3)

    i) DMF, POCl3

    ii) aq. Na2CO3

    CHO

    O

    O

    QII) Complete the following systemic diagram:

    A


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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-HEthe students are able to do the the following chemical transformations:

    1- Heterocycles to another heterocycles in a direct pathway:


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    2- Three-membered to four-membered heterocycles via

    aliphatic compounds and vis versa:


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    3- Heterocyclic derivative to another hetercyclic derivative:

    Example:


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    4-Aliphatic compound to another aliphatic compound

    via heterocycle:


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    5- Heterocycles to homocycles:


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    6- Design synthesis of any target heterocyclic system via

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


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • Conclusion:

    • After the experimentation of SATLHC in Egypt we reached to the following conclusions:

    1)SATLHCimproved the students ability to view (HC) from a more global perspective.

    2)SATLHChelps the students to develop their own mental framework at higher-level cognitive processes (application, analysis, and synthesis).

    3)SATLHCincreases students ability & enthusiasm to learn HCin a greater context.

    • 4)SATLHChelp students to view the pattern of pure and applied heterocyclic

    • chemistry rather than synthesis and reactions of heterocycles.

    5)SATLHCincreases the ability of students to think systemically.

    6)SATLHC enhances the students mental skills towards building

    target heterocyclic systems via Retro-Synthetic Analysis.


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    • 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).


    The systemic approach to teaching and learning heterocyclic chemistry satlhc

    THAK YOU

    FOR YOUR

    ATTENTION


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