Organic Chemistry Fourth Edition - Instructor Pages：有机化学第四版-导师页.pptVIP

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Organic Chemistry Fourth Edition - Instructor Pages：有机化学第四版-导师页.ppt

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Organic Chemistry Fourth Edition - Instructor Pages：有机化学第四版-导师页

24.6Sources of Phenols Phenol is an important industrial chemical. Major use is in phenolic resins for adhesives and plastics. Annual U.S. production is about 4 billion pounds per year. IndustrialPreparationsof Phenol Laboratory Synthesis of Phenols from arylamines via diazonium ions 24.7Naturally Occurring Phenols Many phenols occur naturally Example: Thymol Example: 2,5-Dichlorophenol 24.8Reactions of Phenols:Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Halogenation monohalogenation in nonpolar solvent(1,2-dichloroethane) Halogenation multiple halogenation in polar solvent(water) Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Nitration OH group controls regiochemistry Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Nitrosation only strongly activated rings undergo nitrosation when treated with nitrous acid Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Sulfonation OH group controls regiochemistry Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Friedel-Crafts Alkylation (CH3)3COH reacts with H3PO4 to give (CH3)3C+ Electrophilic Aromatic Substitution in Phenols Halogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation 24.9Acylation of Phenols Friedel-Crafts Acylation under Friedel-Crafts conditions, acylation of the ring occurs(C-acylation) O-Acylation in the absence of AlCl3, acylation of the hydroxyl group occurs (O-acylation) O- versus C-Acylation O-Acylation is kinetically controlled proc