有机化学(下)复习题_完成反应式答案.pdf

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1、专业.专注有机化学有机化学 II II 总复习总复习（一一）完成反应式解答完成反应式解答O O2 2C C2 2H H5 5CHCOOHCHCOOHOHOHH H+C C2 2H H5 5O OO OO OC C2 2H H5 5O OHOOCHOOCCH=CHCHCOOHCH=CHCHCOOHCOOHCOOHO OCOOHCOOHHOOCHOOCHOOCHOOCO OO OO OO OCOOHCOOHCOOHCOOHCHCH2 2C C6 6H H5 5COONa +COONa +COCO2 2NaNa+CHCHCHCH2 2BrBrBrBrCHCH2 2BrBrC C6 6H H5 5CO

2、OCHCOOCH2 2CH=CHCH=CH2 2BrBrO OCHCH2 2OCOCCHCH3 3CHCH2 2CHCH2 2COOHCOOH+BrBr2 2H HCOOHCOOHClClH HP PBrBrCHCH3 3CHCH2 2CHCOOHCHCOOHH HOHOHOHOH-H H2 2O OCHCH3 3CHCH2 2CHCOOHCHCOOHPb(OAc)Pb(OAc)4 4,I,I2 2CClCCl4 4I IClClH HRONaRONaO OO OO OO OO O2 2N NC CClCl+H HN NO OC C2 2H H5 5OHOHO OO ONaOHNaOHH H2

3、 2O OO OOCOC2 2H H5 5OHOHC C2 2H H5 5OHOHH H+O OO O2 2N NC CN NOCOC2 2H H5 5OCOC2 2H H5 5CHCH3 3O OCHCH3 3CHCH3 3O ON NH HO OCHCH3 3O O+CHCH3 3NHNH2 2CHCH3 3O OC C2 2H H5 5OHOHC C2 2H H5 5ONaONaH H2 2O ON NH HO OOHOH NHCHNHCH3 3CHCH3 3O OOHOHOCOC2 2H H5 5LiAlHLiAlH4 4.学习参考.专业.专注O O(1)(1)LiAlHLiAlH4

4、4O O(2)(2)H H3 3O O+COClCOClClClCHCH2 2OHOHCHCH2 2OHOHH H2 2,Pd/BaSO,Pd/BaSO4 4硫喹啉ClClNaNaC C2 2H H5 5OHOHH H+CHOCHOO OCHCH3 3CH=CHCHCH=CHCH2 2CHCH2 2COCCOC2 2H H5 5COOCHCOOCH3 3(CH(CH2 2)1212COOCHCOOCH3 3NaNa二二 甲甲 苯苯CHCH3 3CH=CHCHCH=CHCH2 2CHCH2 2CHCH2 2OHOHO OH H+(CH(CH2 2)1010OHOHCOOCCOOC2 2H H5

5、5(CH(CH3 3CHCH2 2)2 2CdCdCOOCCOOC2 2H H5 5COCHCOCH2 2CHCH3 3CHCH3 3CHCH2 2COCHCOCH3 3乙醚乙醚H H/H/H2 2O O+COClCOCl(CH(CH3 3)2 2CuLiCuLiCHCH3 3CHCH2 2COClCOCletheretherO OO O+C C2 2H H5 5MgBrMgBrOHOHC C2 2H H5 5HOCHHOCH2 2CHCH2 2CHCH2 2CHCH2 2CCCC2 2H H5 5CNCNO OC C6 6H H5 5MgBrMgBrH H/H/H2 2O O+C CO OC

6、OOCCOOC2 2H H5 5CHCH2 2COCHCOCH2 2CHCH3 3COOCCOOC2 2H H5 5O OCOOCCOOC2 2H H5 52 2COOCCOOC2 2H H5 5+CHCH3 3NaOCNaOC2 2H H5 5O OC C2 2H H5 5ONaONaO OO OCOOCCOOC2 2H H5 5CHCH3 3COOCCOOC2 2H H5 5COCHCOCH2 2COOCCOOC2 2H H5 5O OOHOH-H H2 2O OH H+O OC C2 2H H5 5ONaONaH H5 5C C2 2OOCOOC O OCHCH3 3CHCH2 2NON

7、O2 2+CHCH2 2=CHCOCH=CHCOCH3 3O O+COOCCOOC2 2H H5 5COOCCOOC2 2H H5 5NaHNaHC C6 6H H6 6NaOCHNaOCH3 3O ONONO2 2O OCHCH3 3CHCHCHCH2 2CHCH2 2CCHCCH3 3COCOOCCOCOOC2 2H H5 5C C2 2H H5 5ONaONa甲甲苯苯(C(C2 2H H5 5O)O)2 2COCOCHCH2 2CNCN+CNCNCHCOOCCHCOOC2 2H H5 5.学习参考.专业.专注O OCHCH3 3+HCOOCHCOOC2 2H H5 5NaHNaHethe

8、retherH H+CHCH3 3O OCHOCHOCHCH3 3CHCH2 2CHCH2 2COOCCOOC2 2H H5 5CHCH2 2CHCH3 3LiLiCHCH CHCH I I3 32 2LDA,THFLDA,THFCHCH CHCH CHCOOCCHCOOC H HCHCH3 3CHCH2 2CHCOOCCHCOOC2 2H H5 53 32 22 25 5+NCCHCOOCNCCHCOOC2 2H H5 5NCCHNCCH2 2COOCCOOC2 2H H5 5C C2 2H H5 5ONaONaCHCH3 3COCH=CHPhCOCH=CHPhCHCHCHCH2 2COCH

9、COCH3 3CHOCHO+CHCH3 3COCHCOCH3 3O OOHOHCHCH3 3CHCH3 3(1)(1)OH/HOH/H2 2O O(2)(2)H H+/CHOCHOClCHClCH2 2COCO2 2C C2 2H H5 5NaOCNaOC2 2H H5 5CHCH3 3O OCOOCCOOC2 2H H5 5O O+ClCHClCH2 2COOCCOOC2 2H H5 5KOC(CHKOC(CH3 3)3 3t BuOHt BuOH1.1.Zn/CZn/C6 6H H6 6+2.2.H HO OCOOCCOOC2 2H H5 51.1.OHOH/H/H2 2O O2.2.H

10、H+/-CHOCHO+BrCHBrCH2 2COOCCOOC2 2H H5 5O OCH=CHCOOHCH=CHCOOHO OCOCO2 2C C2 2H H5 5C C2 2H H5 5(1)(1)OHOH /H/H2 2O O(2)(2)H H+-O OO OO OC C2 2H H5 5C C2 2H H5 5OC(CHOC(CH2 2)4 4COCCOC2 2H H5 5NaOCNaOC2 2H H5 5COCO2 2C C2 2H H5 5(1)(1)NaOCNaOC2 2H H5 5(2)(2)BrCBrC2 2H H5 5O O+对对 甲甲 苯苯 磺磺 酸酸甲甲 苯苯N N(1)

11、(1)ClCHClCH2 2CH=CHCH=CH2 2(2)(2)H H3 3O O+O OCHCH2 2CH=CHCH=CH2 2N NH HO ONHNHKOH(s)KOH(s)O OO ON N-K K+O OPhCHPhCH2 2BrBrO ON NCHCH2 2O OH H2 2O OOHOH-CHCH2 2NHNH2 2H H3 3C CH HPhPhC CC CO ONHNH2 2H H3 3C CBrBr2 2/OH/OHH HPhPhC CNHNH2 2O ONHNHO ONONO2 2BrBrBrBrZn/OHZn/OHNHNHNHNHBrBr.学习参考.BrBr2 2/O

12、H/OHNHNH2 2COOCOO-BrBrH H+H H2 2N NBrBrNHNH2 2专业.专注C C6 6H H5 5CONHCONH2 2O OCHCH2 2CClCClP P2 2O O5 5C C6 6H H5 5CNCNCHCH2 2N=C=ON=C=OO OCCCC HNHN2 2NaNNaN3 3CHCH3 3OHOHCHCH2 2NHCOOCHNHCOOCH3 3CHCH2 2COOHCOOHCOCO2 2H HSOClSOCl2 2CHCH2 2N N2 2AgAg2 2O OH H2 2O OCHCH2 2NHCHNHCH2 2CHCH3 3O O2 2N NCHCH

13、2 2NHCOCHNHCOCH3 3H H2 2/Pt/PtH H2 2N NCHCH2 2NHCOCHNHCOCH3 3(1)(1)LiAlHLiAlH4 4H H N N2 2(2)(2)H H2 2O OO O+CHCH3 3CHCH2 2NHNH2 2H H2 2/Pt/Pt压力压力，CHCH3 3N NNHCHNHCH2 2CHCH3 3H HNHCHNHCH3 3HCHO/HHCHO/H+mannich reactionmannich reactionO OO OH HOHOHCHCH2 2NHNH2 2HNOHNO2 2O ONaNONaNO2 2HClHClO OOHOH NH

14、NH2 2CHCH3 3COOCHCHCOOCHCH2 2CH(CHCH(CH3 3)2 2C(CHC(CH3 3)3 3H HCHCH3 3CHCH3 3CHCH2 2C CC CD DH HBrBr。500 C500 C(CH(CH3 3)3 3C CH HH HCHCH3 3CHCH3 3CHCH2 2C CC CC=CC=CH HCH(CHCH(CH3 3)2 2O OOCCHOCCH3 3H HD D。500 C500 CCHCH3 3CHCH3 3CHCH2 2C=CC=CH HD DCHCH3 3COOCOOCHCH3 3CHCH2 2CHCH2 2CHCHN(CHN(CH3 3

15、)3 3OHOHCHCH3 3CHCH3 3CHCH2 2CHCH2 2CH=CHCH=CH2 2CHCH3 3CHCH3 3CHCH3 3CHCH3 3+N(CHN(CH3 3)3 3OHOHCHCH2 2CHCH3 3N(CHN(CH3 3)2 2CHCH3 3.学习参考.CHCH2 2CHCH3 3H H2 2O O2 2N(CHN(CH3 3)2 2O O-CHCH3 3+。200 C200 CCHCH2 2CHCH3 3CHCH3 3专业.专注CHCH3 3CHCH3 3I IN NH H过量过量AgAg2 2O OH H2 2O OCHCH3 3+CHCH3 3N N+CHCH3

16、3N NCHCH3 3OHOH-CHCH3 3CHCH3 3NaOHNaOHH H2 2O OHOHON=NN=NClClCHCH3 3N NNClNCl+HOHOClClCHCH3 3CHCH3 3CHCH3 3CHCH3 3O OC C2 2H H5 5CHCH3 3O OCHCH3 3CHCH3 3C C2 2H H5 5()()CHCH3 3O O2 2C C.CHCH3 3C C2 2H H5 5COCO2 2CHCH3 3()()COCO2 2CHCH3 3COCO2 2CHCH3 3H HH HC C2 2H H5 5CHCH3 3COCO2 2CHCH3 3COCO2 2CHC

17、H3 3H H+COOCHCOOCH3 3CHCH3 3CHCH2 2N N2 2+CHCH3 3OCOCOCOCCCOOCHCCOOCH3 3N NN NCOOCHCOOCH3 3N N+CHCH2 2=CHCOOCH=CHCOOCH3 3O OCHCH3 3OOCOOCN NO OOCOC2 2H H5 5OCOC2 2H H5 5OCOC2 2H H5 5HOHOHOHOO OCHCH2 2CH=CHCH=CH2 2CHCH3 3CHCH3 3O O+CHCH3 3OOCOOCC CC CCOOCHCOOCH3 3O OCHCH3 3COOCHCOOCH3 3COOCHCOOCH3 3C

18、HCH3 3.学习参考.专业.专注+HCHOHCHOS SCOOHCOOHS S+BrBr2 2HCl/ZnClHCl/ZnCl2 2S SCHCH3 3COCO2 2H H25 C25 CH H2 2SOSO4 4。25 C25 Co oCHCH2 2ClClCOOHCOOHBrBrS SS SSOSO3 3H HS SN NH HN NN NH H+CHCH3 3I IN NI I-CHCH3 3CHCH3 3(1)(1)NaNHNaNH2 2(2)(2)PhCOClPhCOCl+CHCH3 3N NCHCH2 2COphCOphN NCHCH3 3NONO2 2HNOHNO3 3N NH

19、 H2 2SOSO4 4N N+N NNONO2 2CHCH3 3C C6 6H H5 5LiLiN NO OH H3 3O O+N NCH=CHCH=CHCHOCHON NOLiOLiCHCH2 2CHCHO OO OClClClClCHCH3 3ONaONaCHCH3 3OH,OH,OCHOCH3 3ClClN NN NCHCH2 2=CHCN=CHCNN NCHCH2 2(COOC(COOC2 2H H5 5)2 2C C2 2H H5 5ONaONaRLiRLiN NCHCH3 3NaNONaNO2 2,HCl,HClN NNHNH2 2N NCuBrCuBrCHCH2 2LiLiCH

20、CH2 2CHCH2 2CHCH2 2CNCNH H3 3+O ON NCHCH2 2COOHCOOHN NBrBrO OCHOCHONCCHNCCH2 2COOCCOOC2 2H H5 5CHCH3 3COONHCOONH4 4O OCCCCH H3 3O ONaNHNaNH2 2CH=CCH=CCNCNCOOCCOOC2 2H H5 5N NCHCH3 3+CHCH3 3N NCH=CCH=C.学习参考.专业.专注CHCH2 2OHOHH HH HO OOHOH+3 3PhNHNHPhNHNH2 2OHOHCHCH2 2OHOHCHCH2 2OCHOCH3 3O OCHCH3 3O OCH

21、CH2 2OCHOCH3 3O OOCHOCH3 3CH=NNHphCH=NNHphHAcHAcH HH HNNHphNNHphOHOHOHOHCHCH2 2OHOHH H3 3O O+OHOHCHCH2 2OCHOCH3 3O OCHCH2 2OCHOCH3 3O OCHCH3 3O O+OHOHO OCHCH3 3O OOCHOCH3 3CHCH3 3O OOCHOCH3 3CHCH3 3O OOCHOCH3 3CHCH2 2OHOHCOOCOO-COOCOO-O OH HOHOHAg(NHAg(NH3 3)2 2+H HOHOHHOHOH HH HOHOHH HOHOH+H HOHOHH HOHOHH HOHOHCHCH2 2OHOHCHCH2 2OHOHCHCH2 2OHOHCHCHCHOCHO2 2OHOHHOHOH HO OH HOHOHOHOHOHOHNaBHNaBH4 4HOHOCHCH COCHCOCHH HOHOH3 33 3OHOHHClHClH HOHOHCHCH2 2OHOH.学习参考.HOHOCHCH3 3O OOCHOCH3 3CHOCHOO OH HO OH HH HO OH HO OCHCH2 2OHOH