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Chapter15 - 1 GOOD MORNING GOOD MORNING 15 Benzene and Aromaticity Based on McMurry’s Organic Chemistry 7 th edition 3 Aromatic Compounds

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Unformatted text preview: 1 GOOD MORNING! GOOD MORNING! 15. Benzene and Aromaticity Based on McMurry’s Organic Chemistry , 7 th edition 3 Aromatic Compounds 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 4 Why this Chapter? Why this Chapter? Reactivity of substituted aromatic compounds is tied to their structure Aromatic compounds provide a sensitive probe for studying relationship between structure and reactivity 5 15.1 Sources and Names of Aromatic 15.1 Sources and Names of Aromatic Hydrocarbons Hydrocarbons From high temperature distillation of coal tar Heating petroleum at high temperature and pressure over a catalyst You must memorize the names on this slide. 6 Table 15-1, p. 518 Know this name! Know this name! Know this name! Know this name! Know this name! Know this name! 7 Naming Aromatic Compounds 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 8 The Phenyl Group The Phenyl Group When a benzene ring is a substituent, the term phenyl is used (for C 6 H 5 r ) You may also see “Ph” or “ φ ” in place of “C 6 H 5 ” “Benzyl” refers to “C 6 H 5 CH 2 r ” 9 Disubstituted Benzenes 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”) 10 Naming Benzenes With More Than Naming Benzenes With More Than Two Substituents Two Substituents Choose numbers to get lowest possible values List substituents alphabetically with hyphenated numbers Common names, such as “toluene” can serve as root name (as in TNT) 11 Benzene has three double bonds but is much less Benzene has three double bonds but is much less reactive than alkenes. WHY? reactive than alkenes. WHY? No Reaction No Reaction Br 2 / CC l 4 Br 2 / CC l 4 Br Br Pd/ H 2 Pd/ H 2 room temp room temp 1 . O 3 2. Zn, H 3 O CHO CHO No Reaction 1 . O 3 2. Zn, H 3 O HBr HBr No Reaction Br Liquid benzene was isolated from lamps using producer gas. Faraday determined formula to be C H The compound had Ring Ring structure structure proposed proposed by Kekule. by Kekule. Kekule’s Kekule’s Dream!...
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This note was uploaded on 04/07/2008 for the course CHGN 222 taught by Professor Cowley during the Spring '08 term at Mines.

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Chapter15 - 1 GOOD MORNING GOOD MORNING 15 Benzene and Aromaticity Based on McMurry’s Organic Chemistry 7 th edition 3 Aromatic Compounds

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