2. Aromatic Compounds
• Formerly used to describe fragrant substances such as
benzaldehyde (from cherries, peaches, and almonds),
toluene (from Tolu balsam), and benzene (from coal
distillate)
• Now used to refer to the class of compounds that contain
six-membered benzene-like rings with three double bonds
Early Days of Organic Chemistry
3.
4. Aromatic Compounds
• Many naturally occurring compounds are aromatic in part
• Steroidal hormone estrone
• Analgesic morphine
• Many synthetic drugs are aromatic in part
• Antidepressant fluoxetine (Prozac)
• Benzene
• Found to cause bone marrow depression
• Leads to leukopenia, or lowered white blood cell count, on
prolonged exposure
Present Days of Organic Chemistry
5. Aromatic substances have acquired nonsystematic names
• Nonsystematic names are discouraged but allowed by IUPAC
• Common name for methylbenzene is toluene
• Common name for hydroxybenzene is phenol
• Common name for aminobenzene is aniline
9.1 Naming Aromatic Compounds
19. Monosubstituted Benzenes
• Systematically named in same manner as other hydrocarbons
• – benzene used as parent name
• C6H5Br is bromobenzene
• C6H5NO2 is nitrobenzene
• C6H5CH2CH2CH3 is propylbenzene
Naming Aromatic Compounds
20. Arenes
• Alkyl-substituted benzenes
• Named depending on the size of the alkyl group
• Alkyl substituent smaller than the ring (6 or fewer carbons),
named as an alkyl substituted benzene
• Alkyl substituent larger than the ring (7 or more carbons),
named as a phenyl-substituted alkane
Phenyl
• Derived from the Greek pheno (“I bear light”)
• Michael Faraday discovered benzene in 1825 from the oily
residue left by illuminating gas used in London street lamps
• Used for the –C6H5 unit when the benzene ring is
considered as a substituent
• Abbreviated as Ph or F (Greek phi)
Naming Aromatic Compounds
22. Disubstituted benzenes
• Named using one of the prefixes
1. ortho- (o-)
• Ortho-disubstituted benzene has
two substituents in a 1,2
relationship
2. meta- (m-)
• Meta-disubstituted benzene has
its substituents in a 1,3
relationship
3. para- (p-)
• Para-disubstituted benzene has
its substituents in a 1,4
relationship
Naming Aromatic Compounds