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CHM247H1 (38)


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Cecilia Kutas

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July 1112 2012 CHM247H1Aromaticity Review and Aromatic Substitution ReactionsWHAT IS AROMATICITYAromatichistorical term refers to fragrant substances usually isolated from natural products o ExamplesVanillinaromaflavour of vanilla derived from vanilla beans a very common aromatic compoundQuininepowerful antipyretic bitter flavour of tonic water isolated from the bark of the Cinchona tree native to the Andes mountains for centuries it was the only effective treatment for malaria because of its powerful antipyretic properties Benzaldehydederived from almonds Today aromatic refers to benzene and its structural derivatives have similar structure and reactivity o Many widelyused drugs contain a benzene ring Zoloft A psychotherapeutic used to treat Viagra Valium depression and panic A vasodilator diazepam a disorders sedative PETROLEUM REFINING by fractional distillationA source of benzene different fractions of the petroleum distillation can be used for different things CHM247H1NOMENCLATUREMany aromatics retain traditional or trivial names IUPAC allows these names MONOSUBSTITUTED BENZENE DERIVATIVESUse benzene as the suffix when the substituent is of low priorityUse benzene or benzo as a prefix with a substituent of high priority iehighly oxidized or highly reactiveoften being highly oxidized results in greater reactivity Highly oxidized N is very electronegative nitrileeasily converted into an acidALKYL SUBSTITUTED BENZENESIf the alkyl group has 6C or less name as benzeneIf the alkyl group has more than 6C name as the parent alkaneNote the difference phenyl vs benzyl vs phenol DISUBSTITUTED BENZENE DERIVATIVESUse o m p to specify spatial relationship between substituents
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