Chapter15 - Aromatic Compounds 15. Benzene and Aromaticity...

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1 15. Benzene and Aromaticity Based on McMurry’s Organic Chemistry , 6 th edition 2 Aromatic Compounds ± Aromatic was used to described some fragrant compounds in early 19 th century ± Not correct: later they are grouped by chemical behavior (unsaturated compounds that undergo substitution rather than addition) ± Current: distinguished from aliphatic compounds by electronic configuration 3 15.1 Sources of Aromatic Hydrocarbons ± From high temperature distillation of coal tar ± Heating petroleum at high temperature and pressure over a catalyst 4 15.2 Naming Aromatic Compounds ± Many common names (toluene = methylbenzene; aniline = aminobenzene) ± Monosubstituted benzenes systematic names as hydrocarbons with – benzene ± C 6 H 5 Br = bromobenzene ± C 6 H 5 NO 2 = nitrobenzene, and C 6 H 5 CH 2 CH 2 CH 3 is propylbenzene
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2 5 The Phenyl Group ± When a benzene ring is a substituent, the term phenyl is used (for C 6 H 5 ) ± You may also see “Ph” or “ φ ” in place of “C 6 H 5 ± Benzyl ” refers to “C 6 H 5 CH 2 6 Disubstituted Benzenes ± Relative positions on a benzene ring ± ortho- (o) on adjacent carbons (1,2) ± meta- (m) separated by one carbon (1,3) ± para- (p) separated by two carbons (1,4) ± Describes reaction patterns (“occurs at the para position”) 7 Naming Benzenes With More Than Two Substituents ± Choose numbers to get lowest possible values
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Chapter15 - Aromatic Compounds 15. Benzene and Aromaticity...

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