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    4 Aromatic Compounds

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    ÉL Fikry
    Aromatic compounds have structures containing benzene rings. Benzene's stability is due to resonance, with electrons being evenly distributed around the ring. Electrophilic aromatic substitution is the most common reaction, involving addition of electrophiles to the benzene ring. Substituents can activate or deactivate the ring by donating or withdrawing electrons. Directing groups influence whether substitution occurs at the ortho, para, or meta positions of the ring.

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    4 Aromatic Compounds

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    ÉL Fikry
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    Aromatic compounds have structures containing benzene rings. Benzene's stability is due to resonance, with electrons being evenly distributed around the ring. Electrophilic aromatic substitution is the most common reaction, involving addition of electrophiles to the benzene ring. Substituents can activate or deactivate the ring by donating or withdrawing electrons. Directing groups influence whether substitution occurs at the ortho, para, or meta positions of the ring.

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    Aromatic compounds have structures containing benzene rings. Benzene's stability is due to resonance, with electrons being evenly distributed around the ring. Electrophilic aromatic substitution is the most common reaction, involving addition of electrophiles to the benzene ring. Substituents can activate or deactivate the ring by donating or withdrawing electrons. Directing groups influence whether substitution occurs at the ortho, para, or meta positions of the ring.

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    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    118 views25 pages

    4 Aromatic Compounds

    Uploaded by

    ÉL Fikry
    Aromatic compounds have structures containing benzene rings. Benzene's stability is due to resonance, with electrons being evenly distributed around the ring. Electrophilic aromatic substitution is the most common reaction, involving addition of electrophiles to the benzene ring. Substituents can activate or deactivate the ring by donating or withdrawing electrons. Directing groups influence whether substitution occurs at the ortho, para, or meta positions of the ring.

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    Aromatic Compounds

    Spices and herbs have long played a romantic role in the course of history. Spices and herbs were among the first natural products studied by organic chemists. Extract pure compounds with these desirable fragrances and flavors and determine their structures, then synthesize in large quantity, at low cost, and without danger Aromatic substances have rather simple structures contain a six-carbon unit C6H5 that passes unscathed through various chemical reactions that alter only the rest of the structure. Benzaldehyde (isolated from the oil of bitter almonds), benzyl alcohol (isolated from gum benzoin, a balsam resin obtained from certain Southeast Asian trees), and toluene (a hydrocarbon isolated from tolu balsam)

    Benzene is the parent hydrocarbon of a class of substances that we now call aromatic compounds, not because of their aroma, but because of their special chemical properties, in particular, their stability.

    Some Facts About Benzene


    Benzene, C6H6, a highly unsaturated structure benzene but does not behave as unsaturated No typical addition reactions of alkenes or alkynes. Instead, benzene reacts mainly by substitution

    The Kekul Structure of Benzene

    Kekul : the single and double bonds exchange positions around the ring so rapidly that the typical reactions of alkenes cannot take place

    Resonance Model for Benzene


    Kekuls model is nearly, but not entirely correct. Two structures differ only in the arrangement of the electrons; all of the atoms occupy the same positions in both structures resonance

    Benzene is planar, carbon atom is at the corner hexagon. C-C : 1.39 , intermediate between typical single (1.54 ) and double (1.34 )

    Orbital Model for Benzene


    Each carbon is sp2-hybridized Hexagonal shape, with H-C-C and C-C-C angles of 120

    Symbols for Benzene

    The symbol with the inscribed circle emphasizes the fact that the electrons are distributed evenly around the ring, and in this sense, it is perhaps the more accurate of the two

    Common names are accepted by IUPAC.

    Nomenclature of Aromatic Compounds

    Monosubstituted benzenes do not have common names accepted by IUPAC : derivatives of benzene

    ortho-, meta-, and para- : o-, m-, and p-

    More than two substituents : numbering the ring.

    The symbol Ar is used foran aryl group,

    The Resonance Energy of Benzene

    Energy (heat) released is about 26 to 30 kcal/mol for each double bond. Kekul structure (1,3,5-cyclohexatriene) should released 84 to 86 kcal/mol Stabilization energy, or resonance energy, is the difference between the actual energy of the real molecule Benzene and other aromatic compounds usually react in such a way as to preserve their aromatic structure and therefore retain their resonance energy

    Electrophilic Aromatic Substitution

    The most common reactions of aromatic compounds involve substitution of other atoms or groups for a ring hydrogen on the aromatic unit

    The Mechanism of Electrophilic Aromatic Substitution

    Halogenation
    Chlorine or bromine is introduced into an aromatic ring by using the halogen together with the corresponding iron halide as a catalyst (that is, Cl2 + FeCl3 or Br2 + FeBr3).

    Nitration

    Sulfonation
    SO3 is a strong electrophile at sulfur

    Alkylation and Acylation


    FriedelCrafts reaction

    Ring-Activating and Ring-Deactivating Substituents

    benzene (left), toluene (middle), and nitrobenzene (right)

    substituents that donate electrons to the ring will increase its electron density and, hence, speed up the reaction; substituents that withdraw electrons from the ring will decrease electron density in the ring

    Ortho,Para-Directing and Meta Directing Groups

    Ortho,Para-Directing Groups

    Meta-Directing Groups

    Halogen are strongly electron withdrawing, they are ring deactivating; Halogen have unshared electron pairs, they are ortho,para directing.

    The Importance of Directing Effects in Synthesis

    Polycyclic Aromatic Hydrocarbons

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