有机合成习题

有机合成习题(总28页)

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合成题(I)

1、由甲苯、丙二酸二乙酯及必要试剂合成：HC3OCH2CH3

COOH2、由C3或C3以下有机物合成：

OO

4、由乙炔、C2或C2以下有机物合成：OH5、由

Br为有机原料合成：

COOCH3CH36、由O合成

OH7、由丙二酸二乙酯合成

COO-N+H

3ICl8、由苯合成IClKI(TM)

ClClClClO9、由邻苯二甲酸酐、丙二酸二乙酯合成：

NC-OHHHOCH10、由C2OH4或C4以下有机物合成：

HOCH

2OH2

叶醇，一种香料) (

解：

O+OCOOEtOCOOEtH2OH+HOOHOHOHOO2 C2H5OHCOOEtCOOEtHOHOCH3CO3H COOEtNa + CHOH25COOEtCH2OHCH2OH

11、由苯甲醛、C3或C3以下有机物合成：

NH2CH2CHCH3

12、由苯、C3或C3以下有机物合成：CHCHCH322OCH3CHCH2COOCH3 OICOOH

13、由C4或C4以下有机物合成：

OH14、由苯、C4或C4以下有机物合成：

C-CH2CH3 CH3

Ph-CH2CHCOOH 15、由苯、C4或C4以下有机物合成：

CH3Br16、由苯或甲苯、C4或C4以下有机物合成：H3C

Br

17、完成转化：

OHClCH2CH2CHOCHCH2CH2CHO

3

18、完成转化：

CHOOHOCHOCH2CH3

H19、完成转化：H3CCH5C6CC2H5HOHCH3C2H5

C=CC6H5HBr20、由甲苯合成：

H3CCN

Ph21、由PhCH=CHCHO PhCH、2ClOOPhOCH3OCH2OHCH2OH

22、由

CH3O

23、完成转化：

OCH3CH2CCH2BrOOCH2CH3

O24、由丙二酸二乙酯合成CH2=CH-CH2-CH-C-OC2H5

CH3O25、由环己醇合成

CH3

OO26、由苯酚、

合成CHO3

4

CH327、由甲苯合成：

BrBrCH2CH3

29、由C3或C3以下有机物为原料合成：

OOHO-C-CH2CH2CH2-C-OH

31、由C4或C4以下有机物为原料合成：

OC2H5HOH32、由乙炔(唯一有机原料)合成：HOH

C2H5HOOCCH2CH2CHCOO- 33、由丙二酸二乙酯合成：

N+H3OOOC-OC2H534、由C3或C3以下有机物为原料合成：

OH36、由C3或C3以下有机物为原料合成：

COOC2H5和

37、由联苯出发合成：

OPh38、由

COOEtCOOEt合成

(可使用PhCH2Br作辅助试剂)

39、由1，3-丁二烯为原料合成：

40、从乙酰乙酸乙酯出发合成：

COOH

OCH3CH3-C-CH-CH2CHO

5

41、完成转化：CH3CH2CH2COOH42、完成转化：CH3CH2COOHCH3CH2COOH

CH3CH2CH2COOH

43、由间硝基甲苯合成：Br

BrCOOH Br44、由丙二酸二乙酯及C3或C3以下有机原料合成：

COOH

Cl45、由萘合成：

NO247、由对溴苯甲醛合成：D

48、由苯、异丙醇、乙酸、乙醇合成：C6H5

CH3C6H5 CH2OHCHCH2CH3 OH49、由丙酸乙酯合成：

OOH

COOEt51、由苯酚为起始原料合成：

OOH52、由“三乙”、丙烯酸乙酯合成：

O6

OHOCH353、由C3或C3以下有机原料合成：CH2CH2CH-CH-C-OCH2CH-OCH2CH3

CH354、由苯、丙酸、二甲胺、乙醇为有机原料合成：

OPhCH3CH3CH2C-O-C--CH-CH2N(CH3)3

CH2C6H5

CH2Cl55、由苯合成

Cl

O56、由苯酚、邻氯苯甲酸合成

BrClC

7

CH31：

CH3+ CH2O + HClZnCl2

CH2Cl( I )CH2(COOEt)2(1) NaOC2H5(2) C2H5BrNaOC2H5-CH(COOEt)2Na+( I )H3CCH2CH(COOEt)2CH2CH3H3CCH2CHCOOHH3CCH2C(COOEt)2CH2CH3CH2CHCH2CH3COCl(1) H2O/H+(2) -CO2SOCl2H3CAlCl3CH2CH3CH3O(TM)

O2解： 2CH3CCH3ONaOH , 减压蒸馏(CH3)2C=CHCCH3

(II)O(1) H2O/H+(2) -CO2CH2(COOEt)2(1) NaOEt(2) ( II )O(CH3)2CCH2CCH3 CH2COOH(CH3)2CCH2CCH3CH(COOEt)2HCNHOOCOCCH3HOHOOCCNCH3- H2OOOCN

H2O/H+OOCOOH

4解：

8

CHCHNa液NH3CHCNaC2H5BrCHCCH2CH3C2H5MgBrCH3CH2CH2lindlarCMgBrO干醚H2OH+CH3CH2CCCH2CH2OH

CH3CH2HC=CBrCH2CH2OHH(TM)CNH2/Pd-BaSO4KMnO45解：

SOCl2NaCNH2OH+COOH

COClBrBrNaOH/醇CHO

COOHBr2/PBrCOOHCH3OH/H+ZnZnBrCHOH2OH+COOCH3干醚COOCH3干醚COOCH3OH- H2OCOOCH3(TM) 6解：

OCH3MgI干醚H2OH+CH3HSO24OHCH3

(1) B2H6(2) H2O2 , OH-CH3HHOHBr2(TM)

7解：CH2(COOEt)2

BrCH(COOEt)2

9

ONHO(1) C2H5ONa(2) (CH3)2CHCH2ClKOHONKOONC(COOEt)2OCH2CH(CH3)2(1) H2O/H+(2) -CO2BrCH(COOEt)2ONCH(COOEt)2O(CH3)2CHCH2CHCOOHNH2COO-即：+

NH3NO28解：

HNO3H2SO4Fe + HClNH2(CH3CO)2ONHCOCH3

NHCOCH3HNO3H2SO4Fe + HClNHCOCH3Cl2NHCOCH3NaNO2+过量HClNO2NHCOCH3CuClClNH2NHCOCH3H2O/OH-ClNH2。0-5 C NH2NaNO2+过量HClN2+ Cl-。0-5 CClClN2+ Cl-ClClBr2ClClClClClClCl

10解：CH2(COOEt)2BrCH(COOEt)2

OOOO(1) NaOC2H5(2) Br(CH2)4BrO(1) NH3 , (2) KOHOBrCH(COOEt)2NKONCH(COOEt)2 O(1) 5%NaOH(2) H+(3) , -CO2NC(COOEt)2OCH2(CH2)3BrBrCH2(CH2)2CH2H2NCHCOOH

10

NaOH分子内SN2NCOOH(TM)

HCHO11解：

+ (CH3CH2CO)2OCH2CHCOOHNH , 3CH3CH2CHNH2CH3(TM)

C2H5COOKCH=CCOOHH2/NiCH3CH2CHCONH2NaOBr/OH-CH3 OCH2CH2CH3ClAlCl3Zn-Hg/HCl12解：

+ CH3CH2C

CH2CH2CH3(1) 混酸(2) Fe+HCl(CH3CO)2OCH2CH2CH3HNO3H2SO4CH2CH2CH3NO2NHCOCH3CH2CH2CH3NO2CN

NH2CH2CH2CH3H2OH+ or OH-NHCOCH3CH2CH2CH3NaNO2+过量HClCuCNNO2NH2。0-5 CNO2N2+ Cl-

CH2CH2CH3H2O/H+Fe + HClCH2CH2CH3NaNO2+过量HClNO2CH2CH2CH3KINH2COOH。0-5 C COOHCH2CH2CH3N2+ Cl-COOHICOOH

11

13解：2 CH3COOC2H5(1) NaOC2H5(2) CH3COOHOCH3CCH2COOC2H5(1) NaOC2H5(2) ClCH2COOEt

OCH3CCHCOOC2H5CH2COOEt(1) 5%NaOH(2) H+(3) , -CO2OCH3CCH2CH2COOH(2) CHOH

25(1) SOCl2OCH3CCH2CH2COOC2H5 NaOC2H5O(1) NaOCH3(2) CH3CH=CHCOOCH3 OOCH3CHCH2COOCH3 (TM) O14解：

Br2Fe(3) CH3COOHBrMg干醚MgBr

OMgBrCH3COC2H5干醚OHH2OH+ZnCl2CCH2CH3CH3+ CH2O + HClCl2PNaCNCCH2CH3CH3CH2Cl

C2H5OH , H2SO4

15解：

CNCH2COOHCH3COOHNaOEtCH2(COOEt)2

PhCH2C(COOEt)2

CH3PhCH2ClPhCH2CH(COOEt)2NaOEtCH3I(1) H2O/H+(2) -CO2PhCH2CHCOOHCH3(TM)

或者：

+ CO + HClAlCl3-CuClCHO(CH3CH2CO)2OC2H5COOK , H+

12

CH=CCOOHH2 (1mol)CH3NiCH2CHCOOHCH3

CH3CH3CH3混酸Fe+HClCH3Br2-H2O16解：

NO2BrNH2NH2 BrBrNaNO2+过量H2SO4BrN2+ HSO4-H3PO2 + H2O。0-5 CH3CBrH3CBr

17解：ClCH2CH2CHOHOCH2CH2OH干HClOClCH2CH2CHOMg干醚 OClMgCH2CH2CHOPhCHO干醚OHH2OH+PhCHCH2CH2CHO

(TM)OCH3CHOCH3OC2H5MgBr干醚18解：

CHOO2 CH3OH干HCl H2OH+HOHCHO

CH2CH3C2H5HTsClOHC2H5C=CHHH3CH5C6CC19解：H3CCCC2H5H

H5C6NaOH 醇 , OSO2C6H4CH3-pCH3C6H5 (注：TsCl = 对甲苯磺酰氯)

13

CH320解：

HNO3H2SO4CH3Br2FeCH3BrFe + HClNO2CH3CuCNCH3Br

NO2CH3NaNO2+过量HClNH2Br

BrN2+ Cl-。0-5 CCNOHH2OH+21

PhCH2ClMg干醚PhCH2MgClHC=CCOOEtPhCH=CHCHOPhCH=CHCHCH2PhPh

PhEtOOC- H2OHPhCOOEtCOOEtPhKMnO4稀、冷 ，OH-PhHOHOPhCOOEtCOOEt

PhCH3COCH3干 HClPhCOOEtCOOEt(1) LiAlH4(2) H2OOOPhOOPhCH2OHCH2OH

22解：OCH3OOAlCl3OOCH3Zn-Hg/HClOCH3

OCCH2CH2COOHOCH3SOCl2AlCl3CH2CH2CH2COOHOCH3O

CH2CH2CH2COClO23解：

CH3CH2CCH2BrHOCH2CH2OH干HCl

CH3CH2CCH2BrOO14

OOCH2(COOEt)2(1) H2O/H+(2) -CO2- H2ONaOC2H5CH3CH2CCH2BrOO

CH3CH2CCH2CH(COOEt)2OCH3CH2CCH2CH2COOHNaBH4OHCH3CH2CHCH2CH2COOH

OOCH2CH3

NaOC2H5CH2=CHCH2Cl24解：CH2(COOEt)2NaOCH3CH3ICH2=CHCH2CH(COOEt)2

CH2=CHCH2C(COOEt)2CH3(1) H2O/H+(2) -CO2CH2=CHCH2CHCOOHCH3

C2H5OHH+CH2=CHCH2CHCOOC2H5

CH325解：OH浓HNO3HOOC(CH2)4COOHC2H5OHH+H5C2OOC(CH2)4COOC2H5

OC2H5ONaOCOOC2H5NaOCH3CH3ICOOC2H5 CH3O(1) H2O/H+(2) -CO2 CH326解：

OCH3OOAlCl3OOCH3Zn-Hg/HClSOCl2AlCl3OCH3O

CH2CH2CH2COOHHO(1) HCCNaCH3OCH=CH2CH=CH2浓H2SO4H2OCH3O

(2) H2/lindlar15

OOCH3O

27解：CH3CH3COClAlCl3CH3Br2FeBrCH3BrZn-HgHClBrCH3Br

CH2CH3(1) H2O/H+(2) -CO2COCH3COCH329解：

CH2(COOEt)2NaOEtCH2=CHCNCH2CH2CN CH(COOEt)2ONaOEtCH3CCH=CH2HOOCCH2CH2CH2COOH

O31解：CH3CCH2COOEt(1) 5%NaOH(2) H+(3) , -CO2OCH3CCH2CH2OCHCCH3 COOEtOCH3CCH2CH2OCH2CCH3稀NaOHNaOEt OOCH3CCH=CH2OCH2CH2CCH3O稀NaOH

O32解：CHCH + H2CHCH 2 Na液NH3lindlarCNaCH2=CH22 CH3CH2BrHBrCH3CH2Br

NaCC2H5CCC2H5

H2lindlarC2H5HC=CC2H5HKMnO4/OH-稀、冷C2H5HOH

HOHC2H516

或者：C2H5CCC2H5Na液NH3C2H5HHC=C(1) CH3CO3HC2H5(2) H2O/H+C2H5HOH

HOHC2H533解：CH2(COOEt)2Br2BrCH(COOEt)2

OOONaOEtCH2=CHCOOEtO(1) NH3 , (2) KOHOBrCH(COOEt)2NKOONCH(COOEt)2 OCH2CH2COOEt(1) 5%NaOH(2) H+(3) , -CO2NC(COOEt)2O CH2CH2COOHH2NCHCOOHHOOCCH2CH2CHCOO- +NH3CH2COOHCNOCH2CH2CH(COOC2H5)2H2OH+34解：

CH3COOHBr2红PCH2COOHNaCNBrO-C2H5OH , H2SO4CH2(COOEt)2

COOC2H5NaOC2H5HOCH2CH2CH

COOC2H5O分子内酯交换OCOC2H5

O36解：

CH3COOHNaOC2H5Br2红PC2H5BrCH2COOHNaCNBrCH2COOHCNNaOC2H5C2H5OH , H2SO4CH3ICH2(COOEt)2

CH3CH2CH(COOC2H5)2CH3CH2C(COOC2H5)2CH3

17

(1) H2O/H+(2) -CO2CH3CH2CHCOOHCH3(1) NaOC2H5(2) CH3COOHNaOC2H5C2H5OH/H+CH3CH2CHCOOC2H5

CH3NaOC2H5CH3IOCH3CCH2COOC2H5CH2=CHCH2Cl2 CH3COOC2H5O OCH2CH=CH2CH3CCCOOC2H5

CH3OHCH3CHCHCH2CH=CH2(TM)

CH3OCCH2CH2COOHZn-HgHClCH3CCHCOOC2H5CH3(1) 5%NaOH(2) H+(3) , -CO2OCH3CCHCH2CH=CH2CH3丁二酸酐AlCl3NaBH437解：

SOCl2

CH2CH2CH2COClAlCl3 OPhLi38解：PPh3 + PhCH2ClPh3P+CH2Ph Cl-OPh3P=CHPh

COOEtCOOEtOCOOEtCH3(1)NaOC2H5(2) H+COOEt(1)NaOC2H5

(2) CH3IPh(1) 5%NaOH(2) H+(3) , -CO2OCH3Ph3P=CHPhCHCH3

或者：

OCH3(1) PhCH2MgCl(2) H2O/H+PhHOCH2PhCH3- H2O CHCH3

18

CH2Cl39解：

+CHCH2CH2Cl(1) H2O/H+(2) -CO2[CH(COOEt)2 ]-Na+

CH2CH(COOEt)2CH2CH2COOH(TM)

40解：

OCH3CCH2COOC2H5NaOC2H5CH3IOCH3CCHCOOC2H5CH3(1) 5%NaOH(2) H+(3) , -CO2NaOC2H5 CH2=CHCH2ClOCH2CH=CH2CH3CCCOOC2H5CH3OCH3CCHCH2CH=CH2

CH3(1) O3(2) Zn , H2OOCH3CCHCH2CHO(TM)

CH341解：

CH3CH2CH2COOH稀H2SO4Br2红PCH3CH2CHCOOHBrKMnO4NaOHH2OCH3CH2CHCOOHOH

CH3CH2CHOCH3CH2COOH

CH2N2 42解：CH3CH2COOH湿Ag 2 OSOCl2OCH3CH2CCHN2CH3CH2COCl

CH3CH2CH2COOH

CH3Fe + HClBr2/H2O43解：

CH3NO2BrCH3BrNH2NaNO2+过量HClNH2。0-5 C

Br19

BrCH3BrN2+ Cl-H3PO2 + H2OBrCH3BrKMnO4BrCOOHBrBrBrBr2 NaOC2H5

44解：CH2(COOEt)2 + BrCH2CH2CH2Br(1) H2O/H+(2) -CO2C(COOEt)2

COOH

45解：

NH2(1) 混酸(2) Fe+HCl(CH3CO)2OHNO3H2SO4NHCOCH3

NO2NH2H2OH+ or OH-NaNO2+过量HClN2+ Cl-CuClCl

。0-5 CNO247解：

BrCHOHOCH2CH2OH干HClNO2OCHOH2OH+Mg干醚NO2OCHOBrBrMg

D2ODCHOCH3CH2MgBrOHDCHCH2CH3

48解：

OHCH3CHCH3CH3COOH+ CO + HClAlCl3,Cu2Cl2CHO

K2CrO7+H2SO4Br2红P

CH3CCH3CH2COOHCNC2H5OH , H2SO4OCH2COOHNaCNBr稀NaOHCH2(COOEt)2

O2 C6H5CHO + CH3COCH3CH2(COOEt)2 C6H5C6H52 NaOEt20

OC6H5EtOOC(1) H2O/H+OZn-HgC6H5(2) -CO2C6H5COOEtC6H5COOHHClC6H5C6H5COOH(TM)49解：

2 CH3CH2COOC2H5(1) NaOC2H5(2) CH3COOHOCH3CH2CCHCOOC2H5CH3OH2OH+HOCH2CH2OH干HCl OOCH3CH3CH2CCHCOOC2H52 CH3MgI干醚 OH

CH3CH2CCHC(CH3)2CH3(TM)51解：

OHH2/NiOH浓HNO3HOOCCOOHH5C2OOC2 C2H5OHH+ , COOC2H5

(1) NaOEt(2) CH3COOHCOOEtOCOOEtONaOEtCH2=CHCCH3COOEtOCH2CH2CCH3 ONaOEt- H2O

OOCH2CH2COOEt(1) 5%NaOH(2) H+(3) , -CO252解：

OCH3CCH2COOEtOCH3CCH2 CH2=CHCOOEt2 NaOEtCH3CCCOOEtCH2CH2COOEtOCH3CCHCH2CH2COOEt CH2CH2COOHCH2CH2COOH2 C2H5OHH+CH2CH2COOEtHOCHCHOH22干HCl

21

OOCH2CH2COOEtNaOEtOOCOOEtO(1) 5%NaOH(2) H+(3) , -CO2CH3CCHCH2CH2COOEtCH3CCH

OCH3C53解：

O稀NaOHOHO(TM)

CH3CH2COOHBr2红PC2H5OHH+CH3CHCOOC2H5BrOHZn干醚CH3CHCOOC2H5ZnBr

CH3CH2CHOH2OH+CH3CO3HCH3CH2CHCHCOOC2H5

CH3H2COCHCH3C2H5OHH+CH2=CHCH3H2CHOCHCH3

OC2H5OHCH3CH2CHCHCOOC2H5+H2CCH3OHHOOCH3+ CH2O + HClZnCl2CHCH3OC2H5CH3H+酯交换

CH3CH2CHCHCOCH2CHOC2H5+ C2H5OH。60 CCH2ClMg干醚CH2MgCl54解：

KMnO4

COClCOOHSOCl2OC6H5CH2CC6H5

C6H5CH2MgCl + C6H5COCl干醚低温22

CH3CH2COOHOC6H5CH2CC6H5干 醚Br2红PC2H5OHH+CH3CHCOOC2H5BrZn干醚CH3CHCOOC2H5ZnBrOHCH3

H2OH+OHCH3C6H5CH2CCHCOOEtC6H5NH(CH3)2C6H5CH2CCHCON(CH3)2

C6H5OPhCH3CHCH2N(CH3)2CH2C6H5LiAlH4OHCH3C6H5CH2CCHCH2N(CH3)2C6H5CH3CH2COOHH+CH3CH2COC55解：

+ CO + HClAlCl3 , Cu2Cl2CHOCl2FeCHO ClCH3Zn-HgHClCl2CH2ClClh ClOH56解：

H2/Ni浓HNO3HOOCCOOH- CO2 , - H2OClCOClO

NaBH4SOCl2Mg干醚MgCl干醚、低温 OCClBr2HOAcOCBrCl

23

合

成题(II)

1、由苯为有机原料合成：

OSO3H解：

浓H2SO4K2CrO7+H2SO4OH(1) Na2SO3H+H2/PtOH

(2) NaOH(S), OMg苯H2OH+OHOHH+O

2、由C3或C3以下有机物合成：

OO(CH3)3C-C-CH2CH2CCH3

O解：2CH3CCH3Mg苯OHOHCH3COCH3CCH2COOEtNaOEtCCH3H+CH3OCH3CCH3OOCHCCH3 COOEtCCH3

CH3CH3Br2HOAcCH3OCH3CCH3CCH2Br(CH3)3CCCH2(1) 5%NaOH(2) H+(3) , -CO2O(CH3)3CCCH2CH2OCCH3

C6H5-CH=CH-C=CH-CH=CH2 3、由苯、苯甲醛、C3或C3以下有机物合成：

C6H5O解：

(CH3CO)2OAlCl3C6H5CHONaOH , OC6H5CCH=CHC6H5

CCH324

CH2=CHCH2MgClOHH2OH+C6H5CCH=CHC6H5CH2CH=CH2- H2O CH2=CHCH=CCH=CHC6H5 (TM)

C6H5 或者：

Ph3PCH2=CHCH2ClOPh3P+CH2CH=CH2 Cl-Ph3P=CHCH=CH2PhLiPh3P=CHCH=CH2

C6H5CCH=CHC6H5CH2=CHCH=CCH=CHC6H5

C6H5

CH24、由苯、C4或C4以下有机物合成：解：

O+OOSOCl2AlCl3AlCl3OCCH2CH2COOHZn-HgHCl(CH2)3COOH

Ph3P=CH2

OPh3P=CH2的制法：Ph3P + CH3IPh3P+CH3 I-PhLi干醚CH2

Ph3P=CH2OCH3H3COOCH35、完成转化：

O

25

OCH3NaOEtOCH2=CHCCH2CH3OCH3OCH2CH2CCH2CH3O

解：

OOCH3NaOHCH3O

6、由苯、甲苯、丙二酸二乙酯、C3或C3以下有机物合成：

CH2COOC2H5CH3CCH2CHCH2CH3

AlCl3 , Cu2Cl2解：CH3CH3COCH3NaOH , + CO + HClCH3OCHO

CH(COOEt)2OCH3CH=CHCCH3CH2(COOEt)2NaOEtCH3CCH2CH CH3(1) H2O/H+(2) -CO2OCH2COOHCH3(1) SOCl2(2) C2H5OHOCH2COOEtCH3

CH3CCH2CHCH3CCH2CHPh3P=CH2CH2CH2COOEtCH3CCH2CHCHO和

CH3CH2OH

7、由解：

BrCH2-C=CHCOOEt合成

CH3CHOBrCH2C=CHCOOEtCH3Zn干醚BrZnCH2C=CHCOOEtCH3 26

OHH2OH+COOEtCOOEt

(1) LiAlH4(2) H2OCH2OH

或者：

BrCH2C=CHCOOEtCH3CHOPh3PPh3PCH2C=CHCOOEt BrCH3+-PhLiPh3P=CHC=CHCOOEt

CH3(1) LiAlH4(2) H2OCOOEt CH2OH

8、用方便易得的原料合成：

O

O解：

+NHCH2对甲苯磺酸 苯 ，N(1) CH3CH2Br(2) H2OCH2CH3

Ph3P=CH2CH2CH3

9、完成转化：

O

解：

2OMg苯OHOHOH+Zn-HgHCl

OH10、由邻苯二酚合成：CH3O

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OH解：

OHCH3I(1mol)NaOHOCH3OHCH2=CHCH2ClNaOHOCH3OCH2CH=CH2

OCH3OH(TM)

CH2CH=CH2OO11、由苯酚、

合成 CHO3

解：

O12、由苯酚合成：解：

OHCHCl3+ NaOHO

OHCHO(CH3CO)2OCH3COOK , OHCH=CHCOOH

OO

13、完成转化：CH3CH2COOH解：

CH3CH2CH2COOH

O14、由C3或C3以下化合物为原料合成：

O

解：

COOH15、由C3或C3以下化合物为原料合成：

O解：2 CH3CCH3Mg苯OHOHCH3CCCH3Al2O3CH2CCH3CH3CCH2 CH3CH328

OHCH2=CHCHOCHOBrZnCH2COOEtH2OH+CHCH2COOEt

(1) 5%NaOH(2) H+(3)  H2OCOOH

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