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Chapter 21-2 - CHEM 262 Wei You Chapter 21 Benzene and the...

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11 CHEM 262 Wei You Chapter 21. Benzene and the Concept of Aromaticity (2)
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Nomenclature Monosubstituted alkylbenzenes are named as derivatives of benzene many common names are retained Toluen e Cumen e Ethylbenzene Styren e Pheno l Anilin e Benzoic acid Anisol e COOH NH 2 OCH 3 OH Benzaldehyde CHO What are IUPAC names for cumene and styrene? 22
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Nomenclature Benzyl vs. Phenyl (Z)-2- Phenyl- 2- butene 4-(3-Methoxyphenyl)- 2-butanone 1-Phenyl- 1pentanone O O H 3 CO Ph Benzen e Phenyl group, Ph- Toluen e Benzyl group, Bn- CH 3 CH 2 - 33 If the alkyl substituent is the same size or smaller than the ring (six or fewer carbons), the compound is named as an alkyl substituted benzene If the alkyl substituent is larger than the ring (more than six carbons), the compound is named as a phenyl substituted alkane
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Disubstituted Benzenes Locate two groups by numbers or by the locators ortho (1,2-), meta (1,3-), and para (1,4-) where one group imparts a special name, name the compound as a derivative of that molecule CH 3 Br COOH NO 2 Cl NH 2 CH 3 CH 3  2-Nitrobenzoic acid ( o -Nitrobenzoic acid )  3-Chloroaniline ( m -Chloroaniline)  4-Bromotoluene ( p -Bromotoluene) m -Xylene 44
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Disubstituted Benzenes where neither group imparts a special name, locate the groups
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