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AROMATIC
COMPOUNDS
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
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
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
BENZENE
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
Naming Aromatic Compounds
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
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
Phenyl-substituting Group
Naming Aromatic Compounds
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
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt
Aromatic Compounds and its Derivativesppt

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Aromatic Compounds and its Derivativesppt