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1、海南大学有机化学重点a.CH3CH2CH=CH2H2SO4CH3CH2CHCH3OSO2OHb.(CH3)2C=CHCH3HBr(CH3)2C-CH2CH3Br1).BH32).HO,OH22H2O / H+c.CH3CH2CH=CH2CH3CH2CH2CH2OHd.CH3CH2CH=CH2CH3CH2CH-CHOH3e.(CH3)2C=CHCH2CH31).O32).Zn,H2OCl2 / H2OCH3COCH3+2OHCH3CH2CHOf.CH2=CHCH2OHClCH2CH-CHOHCla.CH3CH2CH2CCHHCl(过量)CH3CH2CH2CH+CH3ClCH3CH2COOH+CH
2、3COOHb.CH3CH2CCCH3+KMnO42CH3c.CH3CH2CCCH3+H2OH2SOHgSO44CH3CH2CH2COCH3+CH3CH2COCHd.CH2=CHCH=CH2+CH2=CHCHOCHOe.CH3CH2CCHHCNCH3CH2C=CH2CNCH3f.O3OCHOCH3Znpowder ,H2OCH3g.H2SOH2O ,4OHh.+CH3CH2Cl2AlCl3CH2CH3+HNO+CH3NO2i.3NOj.+KMnOH+24COOHk.CH=CH2CH+Cl2ClClCH2Cle.CH(CH3)2高温+Cl2C(CH3)2CH3a.HBrCH3Brb.+Cl2高温C
3、lClc.+Cl2Cl+ClClBrC2H5CH2CH3d.+Br2FeBr3BrC2H5+a.Br2FeBr3BrHNOH2SOBr234BrNO2b.HNOH2SOCH334NO2Br3FeBrCH3Cl2 Cl2FeCl3O2Nc.ClCH3d.+Cl2FeCl3CH3KMnO4COOHClCH3e.KMnO4ClCOOHCOOHCl2FeCl3ClCH3BrBrCH3f.HNOH2SOCH3g.Br2FeBr334H3CNO2Br22FeBr3NOCH3KMnO42COOHHNOH2SO34COOHBrBrNOBr2OHa.CrO3.Py2Ob.CH3CH2CH2OH浓H2SO4CH3
4、CH=CH2Br2CH3CH-CHBrBr2KOH / EtOHCH3CCHc.ACH3CH2CH2OHH+Na(CH3)2CHBrCH3CH2CH2OCH(CH3)2BrHBrCH3CHCH3CH3CH=CH2B.CH3CH2CH2OHH+HBrCH3CH2CH2BrOHONaNa3CH3CH=CH2HBrHOHH+CH3CHCHCH3CHCH3CH3CH2CH2BrT.MOHCH3CH2CHCH3d.CH3CH2CH2CH2OHOHCH3CH2CH2CH2BrOHCH3CH2OHNaOHCH3CH2CH=CH2HOHH+e.浓H2SO4SO3Hf.CH2=CH2H2O+Cl稀 冷KMnO4
5、CH2-CHOHOH22OHOCHHOCH2CH2OCH2CH2OCH2CH2OH2ClCH2CH2OHNaOH2CH2OCH2CH2OCH2CH2OHClCH2CH2OHg.CH3CH2CH=CH21)B2H6,Et2O2)H2O2,OHNaOHOCH3CH2CH2CH2OHh.ClCH2CH2CH2CH2OHa.b.(CH3)2CHCHOHOCH2CH2OH+HBr无水ZnCl2(CH3)2CHCH2CH2Br+3HClClc.+CH2CH2OCH3HI(过量)+CH2CH2CH3d.Oe.+CH3HI(过量)+NaOC2H5(CH3)2CHBr(CH3)2CHOC2H5+CH3CH=CH
6、2f.CH3(CH2)3CHCHOH3KMnOOH4CH3(CH2)3COCH3g.CH3COCHOH3CH2CH3HIO4 CH3COOH+CH3CH2CHOCHh.OHOHOHHIO4CH3COCHOHBr2CH2CHOBrCCl4 , CS2中单取代CH3i.+CH3Br2j.CH3(CH2)2CHOHCH2CH3浓H2SO4分子内脱水CH3CH2CH=CHCH2CH3+CH3CH2CH2CH=CHCH3Na.CH3COCH2CH3OH+H2NOHOHCH3CCH2CH3b.Cl3CCHOH3C+H2O+Cl3CCHOHKMnOH4+c.CHOHOOCCOOHOHd.CH3CH2CHO稀
7、NaOHCH3CH2CH-CHCHOCH3CH3e.C6H5COCH3+CH3C6H5COH+C6H5MgBrC6H5COMgBrHH2OC6H5f.O+H2NNHC6H5C6H5NNHC6H5g.(CH3)3CCHO浓NaOH(CH3)3CCH2OH无水HCl+(CH3)3CCOOHOOh.O+(CH3)2C(CH2OH)+2i.O+K2Cr2O7HHOOC(CH2)3COOHj.CHOKMnO室温4COOH+CHClOk.COl.CCH3+Cl2H+CH3Cl2,H2OOHCOOHOC3CH2ClClCl2CH2COCH3OHCH3m.CH2=CHCH2CH2COCH3+HClCH3-CH
8、CH+n.CH2=CHCOCH3+HBrBrCH2CH2COCH3l.o.2CH2=CHCHOCOOH+HCNHOCH2CH2OHNCCHH2CH2CHO+COOCH+OCH2=CHCHOH2CH2OOCm.p.C6H5CHO+CH3COCHLiAlH稀4NaOH3CNC6H5CHCHOH2C-CH3COOHn.CH2OHHCOOH+OHH+HCOOOo.CH2CH2COOCCH2CH2COOCCONH2H52H5NaOC2H5COOC2H5p.N2COOOH+NHNONHO3q.CH2(COOC2H5)2+H2NCONH2NHOa.C2H5OHOCrO3.(Py)2CH3CHOHCNCH3C
9、HOHCNOH+H2OCH3CHCOOHOHb.CCl无水AlCl3Cc.OHgNaBH+4H2O稀CH3CHOOHOHd.HCCH,H+CH3CH=CHCHOH2 / NiCH3CH2CH2CH2OHOHH2OCH3e.Cl2光f.CH3CH=CHCHOH3O+CH2ClMgEt2OCH2MgCl1)CH3COCH2)H+3CH2CCHCHO33OHOHO无水HClCH3CH=CHCHO稀冷KMnOOH4CH3CH-CHCHOHOHOCH3CH-CHCHOOHOHMgCH3CH2CH2BrEt2O1)HCHO2)H+g.CH3CH2CH2OHHBrCH3CH2CH2MgBrCH3CH2CH2
10、CH2OHa.Na2Cr2O7-H2SO4COOHCOOHCOOH+COOHb.(CH3)2CHOH+H3CCOClH3CCOOCH(CH3)2c.HOCH2CH2COOHLiAlH4HOCH2CH2CH2OHd.NCCH2CH2CN+H2ONaOHOOCCH2CH2COOH+HOOCCH2CH2COOHe.CH2COOHOCH2COOHBa(OH)2CH3无水AlClCH3CHCOCH33f.CH3COCl+3+COCH3g.(CH3CO)2O+OHOCOCH3h.CH3CH2COOC2H5NaOC2H5CH3CH2COCHCOOCCH32H5i.j.k.CH3COOC2H5+CH3CH2C
11、H2OHH+CH3COOCH+ CO2Cl2CH2CH3+C2H5OHCH3CH(COOH)2CH3CH2COOHHClCOOH+COOHl.2COOH+HOCH2CH2OHH+COOCH2CH2OOCm.COOHn.a.LiAlH4CH2OHCNOHH+HCOOHO+HCNOHH+HCOOCOOHOHo.b.CH2CH2COOC2H5NaOC2H5CNCH3CH2CH2BrCH3CH2CH2CNCH2CH2COOC2H5CONH(CH3)2CHOHCH3N2H2OOHCOOCH2O+H52CH3CH2CH2COOHc.p.CrO3.(Py)2HCN(CH3)2COCOOCOOHNCOOH(C
12、H3)2CCNH+(CH3)2COHCOOHOHKMnO+NHO3OHOOOOH2OOd.q.CH2(COOCCH32H5)24+H2NCONH2COOHCOOHBa(OH)2HNNHOOOe.(CH3)2C=CH2HBr(CH3)3CBrMgEt2O(CH3)3CMgBr(CH3)3CCOOH2)H/ H2O+ 1)CO2f.CH3BrAlCl3CH3KMnO4COOHBr2FeBrCOOHg.HCCHHOH2O+,Hg2+CH3CHOKMnO4CH3COOHCH3CH2OHH+CH3COOC2H5h.OHNO3h.i.CH3CH2COOHHNOHOOC(CH2)4COOHO3HOOC(CH
13、42)4COOHOHBrMgCH3CH2CH2BrLiAlHi.CH3CH2COOHOHLiAlHCH3CH2CH2OH4CH3CH2CH2OHKMnO4HBrCH3CH2CH2BrCH3CH2CH2CH2COOHMgEt2OEt2OCH3CH2CH2MgBrCH3CH2CH2MgBr或或j.CH3CH2CH2CH2CH2OH1)EtONa2COOC2H51)EtONa2)CH3CH2CH2BrCH3COCH2COOC2H52)CH3CH2CH2BrHCOCHCH3+O+CH3CH2CH2CH2CH2OHKMnO4CH3CH2CH2CH2COOHCHCOOC2H5CH3COCH3COCH2CO
14、OHCH2CHCOOC2CH23H5CH2CH2CH3H3O+浓OH浓OHCH3(CH2)3COOHCH3(CH2)3COOHj.CH3COOHCl2CH3COOHEtOHO+EtOHH,+H,ClP2PCH2COOHCNCHCl2COOHClCH2(COOC2H5)2CNCHCN2COOHCNH3O+CH2(COOCNH32H5)2k.k.OOCH2COONH4OONH3CH2COONH4CH2CONH2CH2CONH2+Ol.CO2CH3l.CO2CH3OHHCOOHHH2OH2OSOCl2+COOHOH(CH3CO)2OCOOH(CH3CO)2OOHCOOHOOCCH3OHm.CH3CH
15、2COOHOHCH3CH2COClOH+OHOOCCH3m.n.CH3CH2COOHCH3CH(COOC2H5)2SOCl1)2OHCH3CH2COClCH3CH2COOHCH3CH2COOCH3CH2COOn.CH3CH(COOC2H5)22)1)H3)2)H+3)CH3CH2COOHa.CH3COCHCOOCCH32H51)稀OH+ 2)H, H2O浓NaOH-CH3COCH2CH3b.CH3COCHCO2CH3CH2COOCH2COOCH2CO2CH3c.CH3CH2CHCOOHOHCOOCHd.COCH3_+ CHCOO + CH3OH_3O_CH3CH2HCOCOCHCH2CH3CO
16、3O稀H+CCH3+ CO2 + CH3OHOe.CH2CH2CHCOOHCHf.HOOCCH33OCH2CH2CH3+ CO22COCCOOHCH3COCH(CH3)2CHg.CH3CH2CHCOOHClh.CH3CHCHOHOi.OCH3j.CH3CH3CH2CCOOHOHk.CH3CH2COCO2H3NaOH-H2OCH3CH2CHCOONaOHCH3CH=CHCOOH2COOHNaOH-H2OCH3CHCH2COONaCH2OH稀H2SO4OCH3CH2CCH3 + HCOOH稀H2SO4CH3CH2CHO+CO2l.CH3CHCOCOCH32HCH3CHCOOHCH3O+COm.CO
17、OHCOOHCOOHOOn.Oo,O1)NaOH,2)HCl,OPOCH3CH2COOH+Cl2CH3CHCOOHCla.BrCHO2(CH2)2CH2CO2HNaOHOOb.CO2CH3EtOCClCH2H52COCH3OCO2CH33O1)稀OH2)H,1)NaOCCH3COCH2COOC2H5+-CH2COCH3CH2COCHc.CH3COOHOCH3CH3CH2OHH+CH3COOC2H5NaOC2H52H52)BrCH2CH2CH2BrCCCOOC2H51)OH2)H+,-CH3COd.CH3COOC2H5NaOC2H51)NaOCCH3COCHCOCH2COOC2H52H53CH3
18、CH3COCHCOOC2H52)BrCH1)NaOC2H52H532H52H52CH3CCOOOCCH3CHCOOCNHFe+HClNHCOCH_1)浓OH,2)H+CH3CHCOOHCH3CHCOOH2)CH3CHCOOCBra.HNO3H2SO4NHb.2NO2(CH3CO)2O3HNO3O2NNHCOCH3H+O2NNH2c.CH3COOHCH3COOHCH3COOHP2O5(CH3CO)2O2NHNH3CH3CONHCH3CONH2SOClNH3CH3COClCH3COO32NH+4CH3CONH2d.CH3CH2OHHClCrO3(Py)2CH3CHO1)CH3CH2MgCl2)H+
19、CH3CH(OH)CHNH22CH3SOCl2CH3CHCHCl2CH3MgCH3CH2ClEt2OCH3CH2MgClCH3CHCH2CH3NH3NHe.NO22NHCOCH(CH3CO)2ONH23f.Fe+HClBr2 ,FeNO2NHNHFe+HClBr2NaNO0-5 C02+HClN2Cl+-+2N弱HNNH2BrCH3BrCH3CH3NaNO0-5 C0BrN2Cl2+-g.HNO3Fe+HClO2NH2NHOH3C-N+HClH3COHNOH-a.(C2H5)3N+CH3CHCHBr3(C2H5)3N+CHCH3CH3Brb.(CH3)3NCH2CH2CH2CH3Cl+NaOH
20、+(CH3)3NCH2CH2CH2CH3+Cl+Na+OHc.CH3CH2COCl+H3CNHCH3CH3CH2CONCH3CH3d.N(C2H5)2+HNO2N(C2H5)2NO灰白色Ag(NH3)2+a.正庚烷1,4庚二烯1庚炔1庚炔褪色正庚烷1,4庚二烯Br2 / CCl4无反应正庚烷1,4庚二烯无反应b.2甲基戊烷2己炔1己炔Ag(NH3)2+灰白色1己炔褪色2甲基戊烷2己炔Br2 / CCl4无反应2甲基戊烷2己炔无反应a.ABC1,3环己二烯苯1己炔Ag(NH3)2+灰白色C无反应B无反应ABBr2 / CCl4褪色AAB环丙烷无反应 KMnO4褪色Bb.A丙烯a.HCCCH2CH
21、2OHOHCH3CCCH2OH a. Ag(NH3)2+ CH2OHCH3 b. FeCl3 CH3CH2OCH2CH3 , CH3CH2CH2CH2OH , CH3(CH2)4CH3 c. 浓H2SO4和K2Cr2O7 d. CH3CH2Br , CH3CH2OH d. 浓H2SO4 后者成烯烃 a.A丙醛沉淀有沉淀Tollen试剂B丙酮2,4二硝基苯肼无沉淀C丙醇无沉淀I2 / NaOH无沉淀D异丙醇黄色沉淀b.A戊醛沉淀ATollen试剂CHI3BB2戊酮无沉淀BI2 / NaOHC环戊酮C无沉淀Ca.CH3CH2CH2COCH2COOCH3(A)显色A溶解，有气体OHNa2CO3B(B)FeCl3无变化BACOOHCH3CHCOOH(C)不显色COHCH3NHa.2(A)HSO不溶A3C2Cl不溶BBNHCHNaOH可溶3(B)ANaOHCOOH(C)显色COOH可溶CFeClD3(D)D不显色OHCAgCl白b.AA分层(CH3)3N HCl(A)AgNO3或者用NaOH(CHCH+32)4NBr(B)AgBr黄B均相
