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Understanding Benzene Derivatives and Nomenclature

Learn about naming conventions, locants, unique names, and properties of substituted derivatives of benzene. Explore examples of substituted benzenes and their distinct features.

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Understanding Benzene Derivatives and Nomenclature

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  1. Substituted Derivatives of Benzene and Their Nomenclature

  2. General Points 1) Benzene is considered as the parent andcomes last in the name.

  3. Examples Br NO2 C(CH3)3 Bromobenzene tert-Butylbenzene Nitrobenzene

  4. General Points 1) Benzene is considered as the parent andcomes last in the name. 2) List substituents in alphabetical order 3) Number ring in direction that gives lowest substituent at first point of difference

  5. Substituents are listed in alphabetical order

  6. Example Cl Br F 2-bromo-1-chloro-4-fluorobenzene

  7. Ortho, Meta, and Para alternative locants for disubstitutedderivatives of benzene 1,2 = ortho(abbreviated o-) 1,3 = meta(abbreviated m-) 1,4 = para(abbreviated p-)

  8. Cl Cl Examples NO2 CH2CH3 o-ethylnitrobenzene m-dichlorobenzene (1-ethyl-2-nitrobenzene) (1,3-dichlorobenzene)

  9. Unique Names Certain monosubstituted derivatives of benzene have unique names

  10. O CH Unique Names Benzaldehyde

  11. O COH Unique Names Benzoic acid

  12. CH CH2 Unique Names Styrene

  13. O CCH3 Unique Names Acetophenone

  14. OH Unique Names Phenol

  15. OCH3 Unique Names Anisole

  16. NH2 Unique Names Aniline

  17. OCH3 OCH3 NO2 Using Unique Names Anisole p-Nitroanisoleor4-Nitroanisole

  18. More Unique Naming Features

  19. The “unique” substituent is given the 1-position; the ring is numbered in the direction that yields the lowest possible number

  20. Easily confused names CH2— OH phenyl phenol benzyl

  21. Examples of Substituted Benzenes

  22. Polycyclic Aromatic Hydrocarbons

  23. Naphthalene resonance energy = 255 kJ/mol most stable Lewis structure;both rings correspond to Kekulé benzene

  24. Anthracene and Phenanthrene Phenanthrene Anthracene resonance energy: 347 kJ/mol 381 kJ/mol

  25. Physical Properties of Arenes

  26. Physical Properties Resemble other hydrocarbons nonpolar insoluble in water less dense than water

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