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Chapter 15

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Barb Morra

CHM 247 CH.18 Benzene andAromaticity • Aromatic substances differ from others in their chemical behaviour. • Aromaticity: The special characteristics of cyclic conjugated molecules, including unusual stability and a tendency to undergo substitution rather than addition reactions on treatment with electrophiles. Aromatic molecules are planar, cyclic, conjugated species with 4n+2 π electrons. 15.1 Sources and Names of Aromatic Compounds • • Above are some of the common names for some aromatic molecules. • Monosubstituted benzenes are names with benzene as the parent name. • Arenes: An alkyl-substituted benzene. • Phenyl: The name for the –C H6u5it when the benzene ring is considered a substituent. A phenyl group is abbreviated as –Ph. • If the alkyl substituent is longer than the ring, it is the parent. • Benzyl: The C 6 5H - 2roup. • Ortho, o-: A naming prefix used for 1,2-disubstituted benzenes. • Meta, m-: A naming prefix used for 1,3-disubstituted benzenes. • Para, p-: A naming prefix used for 1,4-disubstituted benzenes. • Numbers should be the lowest possible combination. 15.2 Structure and Stability of Benzene • Benzene reacts with Br 2o give the addition product, but never the substitution product. • Benzene is a planar molecule with all the carbon atoms being sp -hybridized and with each p orbital being perpendicular to the plane. • Each p orbital overlaps its neighbour’s p orbital leading the electrons to be able to move freely around the entire rings. This gives benzene a lot of stability from resonance. 15.3 Aromaticity and the Hückel 4n+2 Rule 2 • Benzene is cyclic and conjugated, stable, planar, sp hybridized, undergoes substitution
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