ORGANIC CHEMISTRY Chapter 21 21 11B Nucleophilic Aromatic Substitution through an Elimination-Addition Mechanism: Benzyne o Chlorobenzene can be converted to phenol by heating it with aqueous naoh in a pressurized reactor at 350C o Bromobenzene reacts with KnH, in liquid ammonia OH 10%NaoH Cu H20 350℃.28MPa Br NH 2 NH +KNH-33°C Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 21.11B Nucleophilic Aromatic Substitution through an Elimination-Addition Mechanism: Benzyne Chlorobenzene can be converted to phenol by heating it with aqueous NaOH in a pressurized reactor at 350°C. Bromobenzene reacts with KNH2 in liquid ammonia. Cl 10%NaOH , Cu 350℃ , 28MPa OH H3O+ Br + KNH2 NH3 33°C NH2
ORGANIC CHEMISTRY Chapter 21 o 2-1odo-1, 3-dimethylbenzene do not react with nanh, CH NCH3 NaNH no substitution NH3(O 2-lodo-1, 3-dimethy benzene o p-Chlorotoluene reacts with nanh, to yield a mixture of p-and m-toluidine CH CH NanH, NH NH 2 p-Chlorotoluene p-Toluidine m-toluidine Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 21 2-Iodo-1,3-dimethylbenzene do not react with NaNH2: p-Chlorotoluene reacts with NaNH2 to yield a mixture of p- and m-toluidine: I CH3 CH3 NH3(l) NaNH2 no substitution 2-Iodo-1,3-dimethylbenzene CH3 Cl CH3 NH2 NH3(l) CH3 NH2 + NaNH2 p-Chlorotoluene p-Toluidine m-Toluidine