15. Benzene and Aromaticity - PowerPoint PPT Presentation

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15. Benzene and Aromaticity

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15. Benzene and Aromaticity Based on McMurry s Organic Chemistry, 6th edition Aromatic Compounds Aromatic was originally used to described some fragrant compounds ... – PowerPoint PPT presentation

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Title: 15. Benzene and Aromaticity


1
15. Benzene and Aromaticity
  • Based on
  • McMurrys Organic Chemistry, 6th edition

2
Aromatic Compounds
  • Aromatic was originally used to described some
    fragrant compounds in early 19th century.
  • Later, aromatic was used for specific chemical
    behavior cyclic unsaturated compounds that
    undergo substitution rather than addition.
  • Current aromatic compounds distinguished from
    aliphatic compounds by a special electronic
    configuration.

3
Aromatic Compounds
  • Aromatic Electronic Configuration
  • a cyclic array of (usually) six pi electrons.

Examples
Note that each double bond contains two pi
electrons, so the three double bonds of benzene
gives six p electrons.
4
Aromatic Compounds
Shorthand for a mixture of isomers

Dont use this method of shorthand!
5
15.1 Sources of Aromatic Hydrocarbons
  • - from high temperature distillation of coal tar
  • - heating petroleum at high temp and pressure w/
    catalyst

6
15.2 Naming Aromatic Compounds
  • Substituted benzenes substitutent name
    benzene Ex C6H5Br bromobenzene
  • C6H5NO2 nitrobenzene C6H5CH2CH2CH3
    propylbenzene

7
15.2 Common Names
  • Many common names for substituted benzenes
  • You should know toluene (methylbenzene)
    phenol (hydroxybenzene) benzoic acid,
    benzaldehyde

8
The Phenyl Group
  • When a benzene ring is a substituent, the term
    phenyl is used for the C6H5? group. You may
    also see Ph or f in place of C6H5
  • (Note that benzyl refers to the C6H5CH2?
    group with 7 carbon atoms)
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