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CHM247H1 (26)
Chapter 15

Aromaticity - Lecture and Textbook Notes Chapter 15, 16

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Cecilia Kutas

CHM247H1Jasmyn Lee Chapter 15 Aromaticity and Aromatic Substitution Reactions151 Sources and Names of Aromatic Compounds Aromatic o Historicallyrefers to fragrant substances usually isolated from natural products o Todayrefers to benzene and its structural derivativesMany widely used drugs contain a benzene ringPetroleum Refining source of benzeneNomenclatureMany aromatics retain traditional or trivial names IUPAC allows these names Monosubstituted benzene derivatives o Use benzene as the suffix when the substituent is of low priorityo Use benzene or benzo as prefix with a substituent of high priorityAlkyl substituted benzenes Alkyl substituted benzenesIf alkyl group has 6C or less name as benzeneAlkyl substituted benzene If alkyl group has 6C or less name as benzene o If alkyl group has 6C or less name as benzene Isopropylbenzene IsopropylbenzeneIf alkyl group has more than 6C name as alkaneo If alkyl group has more than 6C name as alkene If alkyl group has more than 6C name as alkane2phenylnonane 2phenylnonane Note difference phenyl vs benzyl vs phenol 1CHM247H1Jasmyn LeeDisubstituted benzene derivatives o Use o m p to specify relationship between substituents Trisubstituted benzene derivatives o When groups are of low similar priority number the substituent groups to reach the lowest sum153 Aromaticity and the Huckel 4n2 Rule Aromaticity of BenzeneCyclic moleculePlanar molecule 2 All carbon atoms sp hybridizedPerpendicular p orbitals overlap sixelectrons delocalizedHuckels rule extends the definition of aromaticity beyond benzeneCyclic planar completely conjugated 4n2electronsApplying Huckels RuleCyclic Planar 4n2 e Completely Conjugated 2
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