第章习题及参考答案 下载本文

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OH14.CH2CH2CO2C2H5CH2CH2CO2C2H5NaOC2H5C2H5OH15.CO2HCNCH3COClNaOH16.NHO(1)LiAlH4(2)H3O+NaEtOH17.C6H5MgBr(C2H5)2OH3O+

A 18.CH3CH2COOC2H5+B19.CH3OCOCH2CH2COClPd/BaSO4,H2110C18.CH3CH2COOC2H5NaEtOH20.CHCOCH653A+B+ClCH2CO2EtNaOEt19.稀OHCHO+(CH)CO32

O20.CH3CHCH2CCH3I2/NaOH 解:

OH COClCONH2BCNH21.ABCH3OHCH2OHO2.ACNBCH3CHCH2CCH3COOH3.5.ACH3CH2CH2OCCH34.CH3CH2CH2CON(CH3)26.H2NCH2CO2CH2CH3.HClOHOCOOEtBCH3CH2CH2C(CH3)2OC7.ACH3CH2CH2CO2CH3O8.ACOOEtOCOOEtBCOOEtOO

9-5

9.AOCO2C2H5BCO10.C6H5HDO11.C6H5OOH12.OOCOCH313.PhCOCH2CONHCH314.CO2C2H5O15.CO2-C6H516.NH17.18.ACH3CH2CH2OHBC2H5OH

OCHCHCCH319.

9.8 完成下列转变。

(1)选用不超过四个碳的有机物为起始原料合成目标化合物。

CH3CH2CH=CCOOHCH3OO 20. NaOOCCH2COONa + 2 CHI3

CH3(2)

CH3

CH3

(3)布鲁芬(Brufen)为抗风湿药。从乙苯出发合成布鲁芬

COOH

(4)将2-氯丁酸转化为3-氯丁酸。 解:(1)

9-6

OH2CH3CH2CHOHO-CH3CH2CHCHCHOCH3Ag2OOHCH3CH2CHCHCOOHCH3H+CCH2CH=CCOOHCH3

(2)

OCH3(1)CH3MgX(2)H2OCH3(1)O3(2)H2OOOCH3OHOHCH3OHCH3CH3H+CH3CH3OCH3?OCH3CH3

(3)

CNClCl2hv-CNZn-HgHClCNCNClOAlCl3OH+TM

(4)

COOC2H5)2C2H5ONaC2H5OHCH3ICH3-CH(COOC2H5)2CH3ONa5OH+NaOHBrCH2CH2BrHBrCH2CH2-CH(COOC2H5)29.9 选择合适的原料,用丙二酸二乙酯法合成下列化合物。

(1)庚二酸 (2)3-甲基丁酸 (3)环丁基甲酸 (4)2-苄基丁酸

CH3CH-CHCOOHOLiAlH4(5)CH2=CH-CHCH2OH

解:

OCH3TsClCH3CH2=CH-CHCH2OTs3CH2CCH2CH3C2H5ONaCH3CH2CCHCH2CHCH=CH2CH3CH3OsO4OOHH2CCHCH2CHC-CH2CH3CH3OH

HCl(gas)O9-7

(1) CH2(COOC2H5)2EtONaEtOHBr(CH2)3Br(EtOCO)2CH(CH2)3CH(COOEt)2T.M.(1)NaOH(2)HCl(1)NaOH(2)HCl(HO2C)2CH(CH2)3CH(CO2H)2(2) CH2(COOC2H5)2EtONaEtOH(CH3)2CHCH(CO2H)2(3) CH2(CO2Et)22EtONa(CH3)2CHCl(CH3)2CHCH(COOEt)2T.M.Br(CH2)3BrCO2EtCO2Et(1)NaOH(2)HClEtONaEtOHC6H5CH2ClT.M.(4) CH2(COOC2H5)2C6H5CH2C2H5EtONaEtOHCH3CH2ClCH3CH2CH(CO2Et)2C(CO2Et)2(1)NaOH(2)HClT.M.

(5)

CH2(COOC2H5)2C2H5ONaC2H5OHCH3ICH3-CH(COOC2H5)2CH3C2H5ONaC2H5OHCH3BrCH2CH2BrBrCH2CH2-CH(COOC2H5)2NaOHH+CH2=CH-CHCOOHOLiAlH4CH3CH2=CH-CHCH2OHOTsClCH3CH2=CH-CHCH2OTs

9.10 选择合适的原料,用由乙酰乙酸乙酯法合成下列化合物。OsO4 CH3CH2CCH2CH3CH3CH2CCHCH2CHCH=CH2C2H(1)3-乙基-2-戊酮; (2) 2,5-己二酮; (3)2-甲基-4-戊酮酸; 5ONaCH3CH3OOH(4) HCl(gas)+CH3CH2CCHCHKMnO2CHC-CH2CH3CH2OH4/HHCHOHCH3CO2H解:3 2CH3CH3OOHH2SO4,CH3CO2C2H5EtONaOCH3COCH2CO2C2H5(1)CH3COCH2CO2C2H5(1)EtONa(1)EtONaCH3COCHCO2EtCH3COC(C2H5)2CO2Et(2)C2H5Br(2)C2H5BrC2H5 9-8