ORGANIC CHEMISTRY Chapter 21 Physical properties o Phenols are like alcohols in being able to form strong intermolecular hydrogen bonds o Phenols have higher boiling points than hydrocarbons of the same molecular weight o a modest solubility in water Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 Physical Properties Phenols are like alcohols in being able to form strong intermolecular hydrogen bonds. Phenols have higher boiling points than hydrocarbons of the same molecular weight. A modest solubility in water
ORGANIC CHEMISTRY Chapter 21 21. 4 Synthesis of Phenols Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 21.4 Synthesis of Phenols
ORGANIC CHEMISTRY Chapter 21 21.4A Laboratory Synthesis HNO Cu,O Ar-NH2 Ar-n2 Ar-OH C 2+ O NH2 OH Br l)NaNO2,H2SO4,0-5℃ Br 2)CuyO, Cu, H2o C Cl(80~92%) 2-Bromo-4-methylphenol Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 21.4A Laboratory Synthesis Ar NH2 HNO2 Ar N2 Cu2O Cu2+, H2O Ar OH NH2 Br Cl (1) NaNO2, H2SO4, 0−5℃ Cu2+ (2) Cu2O, , H2O OH Br Cl (80 ∼ 92%) 2-Bromo-4-methylphenol
ORGANIC CHEMISTRY Chapter 21 214B Industrial Synthesis 1. Hydrolysis of Chlorobenzene dow Process) OH 350℃ HC +2 NaoH (high pressure) 2. Alkali fusion of sodium benzenesulfonate SO2H SOnA ONa OH NaoH NaoH(s) H 350℃C Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 21.4B Industrial Synthesis 1. Hydrolysis of Chlorobenzene (Dow Process) Cl + 2 NaOH 350℃ ONa (high pressure) HCl OH 2. Alkali Fusion of Sodium Benzenesulfonate SO3H SO3Na NaOH(s) 350℃ ONa OH NaOH H+
ORGANIC CHEMISTRY Chapter 21 3. From Cumene Hydroperoxide CH(CH3)2 H3PO4 chch=ch 250°C, pressure Cumene异丙苯 CH CH2-c-o-oh OH HrO 95~135℃ 50~90℃ Ch3-C-CH Cumene hydroperoxide Phenol Acetone 异丙苯过氧化氢 Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 3. From Cumene Hydroperoxide CH3CH CH2 + CH(CH3)2 95~135℃ C O OH 50~90℃ OH + CH3 C CH3 O 异丙苯 异丙苯过氧化氢 H3PO4 250°C, pressure Cumene CH3 CH3 O2 H3O Cumene hydroperoxide Phenol Acetone