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  • Benzene Synthesis Page 51-53

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    Ung Hh
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    The document discusses the step-by-step synthesis of a product using various substituents on a benzene ring. It first attaches -NO2 to the ring, then -Cl, followed by -CH(CH3)2. Finally, it reduces the -NO2 to -NH2. The key steps are: 1) Attaching -NO2 first since it is a meta director, allowing attachment of -Cl to the meta position. 2) Adding -Cl, which is a weaker director than -CH(CH3)2. 3) Attaching -CH(CH3)2 using an alkene. 4) Reducing -NO2 to -NH2 to

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    organic chemistry

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    benzene synthesis page 51-53

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    The document discusses the step-by-step synthesis of a product using various substituents on a benzene ring. It first attaches -NO2 to the ring, then -Cl, followed by -CH(CH3)2. Finally, it reduces the -NO2 to -NH2. The key steps are: 1) Attaching -NO2 first since it is a meta director, allowing attachment of -Cl to the meta position. 2) Adding -Cl, which is a weaker director than -CH(CH3)2. 3) Attaching -CH(CH3)2 using an alkene. 4) Reducing -NO2 to -NH2 to

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    © All Rights Reserved
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    13 views3 pages

    Benzene Synthesis Page 51-53

    Uploaded by

    Ung Hh
    The document discusses the step-by-step synthesis of a product using various substituents on a benzene ring. It first attaches -NO2 to the ring, then -Cl, followed by -CH(CH3)2. Finally, it reduces the -NO2 to -NH2. The key steps are: 1) Attaching -NO2 first since it is a meta director, allowing attachment of -Cl to the meta position. 2) Adding -Cl, which is a weaker director than -CH(CH3)2. 3) Attaching -CH(CH3)2 using an alkene. 4) Reducing -NO2 to -NH2 to

    Copyright:

    © All Rights Reserved
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    of 3

    b) As for the second example, all -Cl , -NH2 and -CH(CH3)2 are

    ortho- ; para- directors. So is it possible to synthesise a


    product at meta- position? The answer lies to -NH2 where it is
    formed from -NO2, a meta director. Therefore, to obtain the
    product of synthesis, -NO2 is first attached to benzene,
    followed by -Cl to the nitrobenzene. This is due to -Cl is
    actually ring deactivate and is not a strong ortho-; para-
    director compare to -CH(CH3)2 (refer to strength of substituent)
    After that, by using an alkene, -CH(CH3)2 is attached. Finally,
    reduction of -NO2 is carried out to form -NH2
    Cl2
    AlCl3

    AlCl3
    + CH3Cl

    CH2CH3
    conc. HCl
    Sn NH2

    NH2
    CH3Cl conc. HNO3 SO3
    AlCl3 CH3 conc. H2SO4 O2N CH3 conc. H2SO4

    O2N CH3 conc. HCl H2N CH3 MnO4- / H+ H 2N COOH


    Sn
    SO3H SO3H SO3H

    conc. HNO3 CH3COCl NO2


    conc. H2SO4 NO2 AlCl O
    3
    CH3 C
    CH3 CH2 CH3 CH2
    CH3CH2CH=CH2 CH CH3 CH
    conc. HCl CH3
    H3PO4
    O Sn
    O
    CH3 C NO2 CH3 C NH2

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