11.7 Substituted Derivatives of Benzene and Their Nomenclature

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11.7Substituted Derivatives of Benzene and
Their Nomenclature
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General Points

• 1) Benzene is considered as the parent andcomes
  last in the name.

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Examples
NO2
Br
C(CH3)3
Bromobenzene
tert-Butylbenzene
Nitrobenzene
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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
  locant at first point of difference

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Example
Cl
Br
F
2-bromo-1-chloro-4-fluorobenzene
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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-)
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Examples
NO2
CH2CH3
o-ethylnitrobenzene
m-dichlorobenzene
(1-ethyl-2-nitrobenzene)
(1,3-dichlorobenzene)
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Table 11.1 (p 407)
Certain monosubstituted derivatives of benzene
have unique names
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Table 11.1 (p 407)
Benzaldehyde
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Table 11.1 (p 407)
Benzoic acid
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Table 11.1 (p 407)
Styrene
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Table 11.1 (p 407)
Anisole
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Table 11.1 (p 407)
Acetophenone
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Table 11.1 (p 407)
Phenol
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Table 11.1 (p 407)
Anisole
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Table 11.1 (p 407)
Aniline
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Names in Table 11.1 can be used as parent
Anisole
p-Nitroanisoleor4-Nitroanisole
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Easily confused names
CH2
OH
phenyl
phenol
benzyl
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11.8Polycyclic Aromatic Hydrocarbons
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Naphthalene

• resonance energy 255 kJ/mol

most stable Lewis structureboth rings
correspond to Kekulé benzene
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Anthracene and Phenanthrene
Phenanthrene
Anthracene
resonance energy
347 kJ/mol
381 kJ/mol
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11.9Physical Properties of Arenes
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Physical Properties

• Resemble other hydrocarbons
• nonpolar
• insoluble in water
• less dense than water