有機化學第15ç« ï&f

有機化學第15ç« ï&f

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Unformatted text preview: 2009/2/26 1 15. Benzene and Aromaticity 苯與芳香族性 Based on McMurry’s Organic Chemistry , 7 th edition OUTLINE Sources and Names of Aromatic Hydrocarbons Structure & Stability of Benzene Structure & Stability of Benzene Aromatiicity and Huckel’s 4 n + 2 Rule Aromatic Ions Aromatic Heterocycles: Pyridine and Pyrrole Why 4n +2? 2 Why 4n +2? Polycyclic Aromatic Compounds Spectroscopy of Aromatic Compounds 2009/2/26 2 Tolu Balsam 南美 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) 類固醇 Cholesterol-lowering drug 2009/2/26 3 Why this Chapter? ¡ Reactivity of substituted aromatic compounds is tied to their structure 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 Hydrocarbons ¡ Coal ¡ From high temperature distillation of coal tar ¡ Petroleum ¡ Heating petroleum at high temperature and pressure over a catalyst 6 2009/2/26 4 PRODUCTION OF COAL TAR PITCH Flushing Liquor Steam 2000 ° F Tar Tar Feed Tank Heater Distillate Stream Distillation Tower gas 200 ° F Coal Coke Oven Liquor Decanter Sludge Decanter Pitch Steam Coal Tar 媒焦油 8 2009/2/26 5 Coke Oven Thermal Cracking 1,095 ° C No catalyst + C 4 CH 2 CH 2 CH 2 CH 3 Many common names 2009/2/26 6 Monosubstituted benzenes systematic names as hydrocarbons with – benzene Alkyl-substituted benzenes 11 Arenes ≦ C6 Alkyl-substituted benzene > C6 Phenyl-substituted alkane 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  ” 12 2009/2/26 7 Disubstituted Benzenes ¡ Relative positions on a benzene ring ¡ ortho- (o) on adjacent carbons (1,2)...
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第15ç« ï&f

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