第九章 醛 酮 醌课件.ppt

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1、CORR键键CORRCO+-醛醛基( )Ar RCOH酮酮基R()Ar()ArRCOCH3COHCH3COCH3CHOCCH3OCHOOCH3COHCH3COCH2CH3CH2CHCOHCH2CHCOCH3CH3COCH3OCCH3COCH2CH3COCH3CH3CH2CHOCH3COCH3CH3CH2CHOCH3COCH3H COCH2COHCOCH2COCH3CH3 CH3CH2CHO丙醛CH3CH2CH2CHO正丁醛异戊醛CH3CH3CHCH2CHOCO二苯(基)酮CH3CCH2OCH3甲(基)乙(基)酮CH2CH3苯(基)乙(基)酮COCH3CH2CHCHOCH312342-甲基丁醛-

2、甲基丁醛)(4CH3CH2CH2CCH3O12352-戊酮 CH3OCH3CCH2CHCH34-甲基-2-戊酮（甲基2戊酮）2-丁烯醛( ， -丁烯醛)14CH3CHCHCHO23CH3CCHCH3CH3CO123454-甲基-3-戊烯-2-酮( -甲基-， -戊烯-2-酮)CHCHCHO1233-苯基丙烯醛( -苯基丙烯醛)CHO苯甲醛COCH3苯乙酮CHCH2CHOCH33-苯基丁醛O环己酮OCH32-甲基环戊酮OHCCH2CH2CHO丁二醛CH3COCH2COCH32 ， 4-戊二酮 CH3COCH2COCHCH3CH35-甲基-2，4-己二酮表表9-1相对分子质量相近的烷烃、醚、醛、酮

3、、醇的沸点比较相对分子质量相近的烷烃、醚、醛、酮、醇的沸点比较CCR(H)OH 羰基的亲核加成反应醛的特有反应羰基的还原反应 活泼氢的反应ORR(H)+-RR(H)RC(CH3)+HCNHOCRH(CH3)OHCNCCH3CH3O+HCNOH-CH3CCNCH3OHHCNOH-H+H+CN-ORR(H)+-RR(H)RR(H)CO+-+Nu-快A+慢CO-NuCNuOAHCHOCORCH3CHORCORRCRH(CH3)O+NaHSO3R(CH3) HCOHSO3Na羟基磺酸钠CRSO3NaHOH(CH3)+SO2+H2ONa2SO3+NaHCO3NaClHClNa2CO3CRH(CH3)OC

4、RH(CH3)O+H3O+Mg(OH)XOMgXRCOHRCCO+-RMgX+无水乙醚 HCHO+CH3CH2CH2MgBr无水乙醚 H+,H2OCH3CH2CH2CH2OHOHCH3CHO+无水乙醚 H+,H2OMgBrCHCH3+CH3CCH3CH3CH2MgBr无水乙醚H+,H2OCH3COHCH3CH2CH3O+RHHNHG-H2OCO+-CNRHGOH HCRHNG()R()R()R+H2OCRH()RO+H2NGCRHNG()R+肟肼腙苯肼苯腙氨基脲缩氨脲H2NOH羟胺OHNH2NO2NO2H2NO2NO2H2NNHH2NNH2O2 ,4二硝基苯肼2 ，4二硝基苯腙CRH()RNC

5、RH()RNCRH()RNNHNNHCRH()RNNHCRH()RCRH()RNNHCONH2H2NNHCONH2+3CH CHOCH3CHH2NOHOHN+NCH3OCH3CH3CCCH3H2N NHNO2NO2NHNO2NO2ROHR干HClCROHRHCO+HO半缩醛缩醛+HO RCRHO ROH干HClCRHO RO R+H2OOC2H5OC2H5CH3CHO+2C2H5OH干HClCH3CHRCHO RO RH+H2O,RCHO+2OHR羟基丁醛（3羟基丁醛）HOHOH+CH3CCH3CHCH2CHOCH2CHO稀OH-+OHCH3CHCHCHOHCH3CHCHCHOH2O2丁烯醛稀

6、OH-CHCH2CHOOH- H2O+CH3CHOCHOCHCHCHOO+Br2H+CH3CCH2BrCH3CCH3OCH3+X2NaOHCX3(H) RCO(H) RCO(H)R(H)RCOCX3+NaOHCOONa+CHX3CH3CCH3O+I2+NaOHCH3COONa+CHI3+NaI+H2OCH3CH2OHCH3CHONaOINaOICHI3+HCOONaR CHCH3OHNaOIRCOCH3RCOONaNaOICHI3+(Ar)RCHO+2(Ar)RCOONH4+2Ag+3NH3H2OOHAg(NH3)2RCHO+2Cu2+NaOHH2ORCOONaCu2O+4H+RCHOH2Pt

7、RCH2OH+H2PtRCORRCRHOHCH3CHCHCHOH2NiCH3CH2CH2CH2OHCH3CHCHCHOCH3CHCHCH2OHLiAlH4CH3CHCHCHOCH3CHCHCH2OHLiAlH4COCH3Zn-Hg/HClCH2CH32HCHO浓NaOHHCOONa+CH3OH2浓NaOHCHOCOONa+CH2OHOCH3OCH3CHOCH2OH+HCHO浓NaOH+HCOONa对甲氧基苯甲醇对甲氧基苯甲醛OO1234561，4-苯醌(对苯醌)OO1，2-苯醌(邻苯醌)OO2,6-萘醌(远-萘醌)123465OO781,4-萘醌-(萘醌)OO1,2-萘醌( -萘醌)O1289

8、O345671010蒽醌9，OOBr2OOBrBrBr2OOBrBrBrBr对苯醌单肟对苯醌双肟OHNOHOONH2OH-NH2OH-ONNOHOO+HClOHOClHOHOHClOO-2H+2HOHOH+OHOHOOOHOOHO维生素K1C (CH2CH2CH2CHCH3CH3CH3)3CH2CHOCH3OOOCH3CCH3(CH2CH)CH2 5CH3CCH3CH2CH2维生素KOOCH32-甲基-1,4-萘醌(维生素K3)亚硫酸氢钠甲萘醌OOCH3SO3Na H2O.OO1， 2蒽醌O，9 10蒽醌O，1 4蒽醌OOOOHOH茜素OOOHOHOHCH3大黄素OOHOOHCOOH大黄酸OThe end.