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Organic chemistry B Chapters 14, 15, 16 Aromatic Compounds By Prof. Dr. Adel M. Awadallah

Organic chemistry B Chapters 14, 15, 16 Aromatic Compounds By Prof. Dr. Adel M. Awadallah Islamic University of Gaza. Aromatic Compounds Hydrocarbons (contain only carbon and hydrogen) Saturated: (Contain only single bonds) Alkanes (C n H 2N + 2 ) Cycloalkanes (C n H 2N )

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Organic chemistry B Chapters 14, 15, 16 Aromatic Compounds By Prof. Dr. Adel M. Awadallah

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  1. Organic chemistry B Chapters 14, 15, 16 Aromatic Compounds By Prof. Dr. Adel M. Awadallah Islamic University of Gaza

  2. Aromatic Compounds Hydrocarbons(contain only carbon and hydrogen) • Saturated: (Contain only single bonds) Alkanes (CnH2N + 2 ) Cycloalkanes (CnH2N ) b)Unsaturated: contain Alkenes: double bonds (,,,CnH2N) Alkynes: triple bonds ((CnH2N - 2) Aromatic: benzene like compounds

  3. Facts about double and triple bonds

  4. Structure of Benzene Benzene is the parent of a class of especially stable compounds called aromatic compounds. It was first isolated by Faraday in 1825 from compressed illuminating gas Different structures were suggested for benzene (C6H6). The regular conjugated hexagon structure was suggested by Kekuli` in 1865

  5. Orbital Model for Benzene

  6. Nomenclature of Aromatic Compounds

  7. Disubstituted Benzene

  8. Assigning Priority • Halogens < alkanes < alkenes < amines < OH < ketone < aldehyde < acid < ester • Examples

  9. Aromatic Compounds in Nature and Health

  10. Aromatic Character • Aromatic compounds are those that resembles benzene: • 1) High degree of unsaturation • 2) Do not undergo addition reactions • 3) Undergo electrophilic substitution • 4) Unusual stability • 5) Cyclic five, six, seven • 6) flat or nearly flat molecules • 7) Delocalized pi clouds must contain a total of • (4N + 2) pi electrons [Hueckel 4n+2 rule] • 8) Protons appear around 7 ppm in NMR

  11. Resonance Energy of Benzene

  12. Hetrocyclic Aromatic Compounds

  13. Rearrangement of carbocations

  14. Rearrangement of carbocations

  15. Reaction of benzene with n-propyl chloride produces isopropyl benzene because of rearrangement

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