1、試 題 庫 五合成題及解答1 .由苯或甲苯及具它無機試劑制備:C00HNO2CH3ab ClC00HLBr N022.CH3COOH。一6CMe33.COOH0-0NO24.OH05. COOHNO2COOHCH3elN；NO2宣年ClBrBrNO26.CH3CH2CH20H - CHsCCH7. CH3CH2CH2OH f CH3CH2CH2OCMCH3)218.8. CH3CH2CH2CH2OH f CH3CH2CH(OH)CH310. CH2=CH2-HOCH2CH2OCH2CH2OCH2CH20HCH3CH2CH=CH2- CH3CH2CH2CH20H12. CH3CH2OH - CH

2、3CH(OH)COOH15. HCmCH - CH3CH2CH2CH20HI.11-,二-CH2CHCH2CH317.OH二-CH2CHCH3OH9.SO3H11.14.OHCOClCO13.一一I . I21 . CH3CH2CH2OH - CH3CH2CH2CH20H22 .寫出由相應的嵌基化合物及格氏試劑合成2-丁醇的兩條路線23 .由苯合成2-苯基乙醇。24 .由甲苯合成2-苯基乙醇25 .00CH3COOC2H5 - HOOCCH-CHCOOEt28.CH3CH319.1:CH2CH2CH2OH20. CH3CH=CHCH3 -CH3CH-CHCHOOHOH26.27.CH3COOH

3、BrCH2(CH2)2cH280H0ICH2COCH3COCH37. CH3CH2CH2OH f CH3CH2CH2OCMCH3)218.29.OCOOHOHCH3CH2CH2BrCH3CH2CH2COOH40._ (CH3)2CCOOH i OH37. CH3CH2COOH f CH3CH2CH2CH2COOH38. CH3COOH f CH2(COOC2H5)230.32.33. (CH)2C=CH2f(CH3)3CCOOH31.(CH3)2CHOH48.42CH3cH20H - - CH3CHCH2CH3NH2NH2NH26一改NONO2NH26r41.NH247.NH2NO246.NH

4、2NO2CH3COCH2COOC2H5合成CH 3cH 2cH 2cH 2cH-CH 3COOHOH55.由CH2（COOC2H5）2合成H3C-CHCOOHiCH2cH=CH256.57.CH3COOHCOOH68.用丙二酸二乙酯合成1, 4環(huán)已二甲酸58.CH3（CH2）3OH-*-CH3（CH2）3SO2（CH2）3C H3CH3-H3ySO2NH：JCH359.60.CH3CH2-： ；-Br61.用丙二酸二乙酯合成1,3-環(huán)戊二甲酸。62.用丙二酸二乙酯合成1,1-環(huán)戊二甲酸。63.用乙酰乙酸乙酯合成CH3COCH2CH2CH2COOH。64.Br65.CH3COCH2BrCH3CO

5、CH2CH2CH2OH66.用乙酰乙酸乙酯合成67.用乙酰乙酸乙酯合成CH3A CH3CH-C-CH3CH30HNH2NO273 .由乙酰乙酸乙酯合成2,5己二酮74 .由丙二酸二乙酯合成3-甲丁酸OH75CH3cH=CH2, CHCH CH3CH2CH2CCH2CH2CH2CH376 .由丙二酸二乙酯合成環(huán)丁基甲酸。77 .由乙醇合成乙酰乙酸乙酯。78.島一K211C-CH079 .0H80 . 1J - I7081 .由乙酰乙酸乙酯合成3-乙基-2-戊酮69.CH3COCH370.由丙二酸二乙酯合成庚二酸71.由乙酰乙酸乙酯合成2,4戊二酮72.95.由1-丁烯合成BrCH2CH2CH2C

6、H2BrOH82 .由丙二酸二乙酯合成83.88.用乙酰乙酸乙酯合成2-甲基-4-戊酮酸94.1NO2CH2CH2CH384.由丙二酸合成2-葦基丁酸。85.由乙酰乙酸乙酯合成CH2CH386.OH6A AOH87.用丙二酸二乙酯合成環(huán)已基甲酸。91.= CH3CH2CH-CHCH3CH3CH396.COOH由92.93.CH3CH2CH2CH2Br97.98.99.100.101.102.103.104.105.106.107.108.109.0CH2CICH2C1OrCH2CH3CH2cH2cH2C1OHCH2cH2cH2cH3OHCH2CH2CH3OHCH2CH=CH2BrI.- lrB

7、rNO2OH(CH3)3CCH2cHCH Br3(CH3)3C、，H.C二C、HCH3由乙快合成3,4二羥基已烷。由環(huán)戊烷合成（其它試劑自選）由甲苯合成H3CCH2CH3Br由苯合成SO3HCOCH3110.以銅鋰試劑合成1-苯基-2-甲基戊烷。（不多于四步）111.以銅鋰試劑合成2-甲基已烷。OHO2NNO2112.以苯為原料合成苦味酸（NO2113.NO2114.由正丁醇合成2-丁醇。115 .由苯酚和兩個碳原子及以下的有機物合成CH3-OC2H5116.五個C原子以下的有機物合成CH3- C-CH3-OH117.以不多于4個C的有機物為原料合成： BrCH2-CH-CH2118.以丙烯為

8、原料合成：Cl Cl BrCH3119 .以丙烯為唯一有機原料合成：CH3-C-CH2CH2CH3OH試題庫之五：合成題答案1 .CHsClKMnO4AlCl3b.HNO3-3H2SO4a.Br2FeBy Cl2FeClNO2心BrCOOHClc.CH36-Cl2FeCl3CH3Cl2FeClClClCOOHCH30 0B2FeByHNOH2SO4NO2Brd.e.Cl2FeCl3KMnO10.CH2=CH2O2/Ag H2O250 C2.O OCHaBr HNO3B/KMnO4AlBr3H2sO4FeBr3COOHNO2Br3.CH30 0(CH3)3CBr KMnO4AlC%COOHCMe

9、34.170 cH2SO4Br2OH-NaNH2乙醇-HBr _ HBr6.CH3cH2cH20H7.CH3CH2CH2OH-Na*-Me2cHBrJA8.CH3CH2CH2CH20HH2SO4H+170 cH2O9.OHOHAl濃H2SO4一100C9.OH令濃H2SO/ 100 c*OHSO3HSO3HB2H611.CH3CH2CH=CH22 612.CH3CH2OH-_ Ag -HCN550CH2O2*OHOH2 2. .CH3CH2CH2CH2OHH2O13.COClC6H6AlCl314.NaBH415.方法一：: :SOSO，OHHgS04OHH2Ni方法二.NaHBrMgH2O,

10、液氨干酸H+15.NaNO2H2SO4H2OCH3CH2CH2OH-HBr*-1M除HCH0.H20ACH3CH2CH2CH20H22.方法一：CH3CHO+CH3CH2MgBr-HCH3cH2cHCH327.CH3COOHEtOH NaOEtCH3COCH2C00Et-COOEt工 x八NaOEJBrCH2CH2CH2BL NaOEJ _ / 乂稀OHL/ COCH3-HBr-HBrCOCH3CH3C0OC2H5Na0EtCH3COCH2COOEtCH3NaOEt藤 BrCHCOOEtjNaOEtLBrCH*濃0H.H+. HOOCCH-CHCOOE-HBrCH3CH316.CH3NBSCH

11、317.十贊CH2cMMgCH3COCH3H2OAH+CH2C CH3OH18.HCHOHCl Zn C，2219.20.CH2C1HCHOHCl Zn Cl2干酸Mg干酬CH3CH2CHOH30+TMCH3CH0H30+3TMO OCH3CH2BrA1C13Mg干酸HCHO0+-3-3TMCH3cH=CHCH3及H2QCH3CH-CHCH3OH OH29.HCNH2OH+30.NaCNH2O2+H+Mg干醛CH2OH2OKMnO4一+H+31.Na2CrO7HCNH2O+H32.KMnO4P2O5 .21.22.方法二：CH3CH2CHO+CH3MgBr6H2OOHH+CH3CH2CHCH3

12、OH23.24.25.26.H2OH+Mg THFCH2CH20HCH3NBSMgHCHOH2OTHFH+BrCH2(CH2)2CH2COOH10HH2O20.CH3CH2CH2OHHBrMg-HCH0CO2cH323Na0Et CH3COCH2BrCH2cH20HuCH3CH2CH2CH2OHCO2cHi3u23稀OH-_HCH2C0CH328.Br2FeCl3OHgSO4KMnO4日OHH2so4H+Na2CrO7Ba(OH)236H2SO4 -ALiAlHAHBr_ Mg _環(huán)氧乙烷H2OKMnO4-+*-APB3NaCN H2O EtOH- - + - -H HH2OCH3COOHH+

13、HNO3Fe + HClH2SO4HBrMgCH3CHOH+Na2CrO7NH3-*-*- nN*Fe Fe+HCl HNO2C6H5NH2Br2一HNO2CuBr - HBr547.48.NaNO2H2SO4H2OH2SO4H3O+Br2H2ONaNO2H3PO2180C HCl 5CrH2O *HNO3Fe+HClBr2NaNO2HClH3PO2+H2OH2sO4 :05C53.HNO3Fe+HCl(CH3CO)2OHNO3H2OHNO2NaNO2HBF4H2SO4A-乙酸 =H:5T-*+NaOC2H5CHaBrNaOC2H5CH2=CHCH2BrH / H?O55.CH2(COOC2H

14、5)2_2TM56.CH3COCH2COOEtEtONaLCH3cH2cH2cH2BrrEtONa)CHsB二酸式分解尸 丁”57.CH3COOH建代，NaCN. EtOH.EtONaCH2(CH2Br)2TMa-取代NaOHH2SO4-2NaBr -CO2NaSH NaOHCH3(CH2)3lHNO358 -1-60Br2CH3CO。Zn / Hg.FeAlCl3HCl EtONa - Na OH丁BrCH2CH2CHMe2酉同式分解IM50.HNO3Fe+HClBrI IK.人 H2SO4廣2NaNO2H2SO4H3PO2+H2O05 c59.H2SO4PCl3H2N CH351.HNO3

15、Fe(CH3CO)2。H2SO4HCl52.61.62.CH3CH2BrAlCl3Br?Fe 2 EtONa尸 2 EtONa一 NaOH廣_ BrCH2CH2Br CH2I2 HCl 2 EtONa _Na OH =七。1 Br(CH2)4BrTM63.EtONa_ * BrCH2CH2COOEt64.HNO3Fe(CH3CO)2OBr2H3O+NaNO2H3PO2H2SO4 HClHCl5CH2O65.HOCH2CH2OHMgOH3O+乙醛66. EtONa - CH3CH2CH2Br EtONaHNOaOH CH3I3ClTMFe+HClH2sO4 FeCl3HNO2-CuBr -HB5

16、 C67.H2SO4NBSH2OBr268. 2EtONa 2EtONa BrCH2cH2Br BrCH2cH2Br NaOH一 HCl_69.70.71.Ni HCl MgCH3COCH3H3O+H2Zn Cl 2干酸A A12 EtONa NaOH2Br(CH2)3B：(EtOCO)2CH(CH3cHe。網(wǎng)2 HCl ATM-EtONa CH3COClOH TMH2O72._HN03FeH2SO4HNO3OH-H2SO4 HCl保護氨基H2SO473.74.EtONaCH3COCH2。OH丁1vl-H2O TMEtONa(CH3)2CHBr Na OH- HCl -TMHBr _ _ _7

17、5.CH3cH=CH2-CH3cH2cH2BrCHKHNaNH2CH3CH2CH2BrNaNH2CH3cH2cH2Br液氨液氨TM762EtONa尸CH2(CH2Br)2 .水解 -2NaBr -CO2TM77.CH3CH2OHKMnO4CH3CH2OHEtONa酯縮合78.HNO3Fe(CH3CO)2OHNO3H2OH2SO4 HCl乙酢H+或OH電79.。3OH-Zn/H2O羥醛縮合-H2OCHO80.Cu250 cHNO3BaOAVA; 脫竣脫水81.1Et0Na尸 EtONa - Na OHH3O+丁2C2H5Br * C2H5Br * 3 *TM82. EtONa Na OHj_ H

18、ClXBrOCOOH83.CH3CH2CH2CHO-322gm 3=CH3CH2CH2CHCH2CH2CH3CrO-，Br2 ATM干酸OH乙酸84.Et0NaCH3CH2Cl - EtONa*c6H5cH2Cl_ Na0H_CHCOOHEtOH曰0H HCl CH3cH2cHe00HCH2c6H585.q EtONa 廣 g 2 EtONa -Na 0H BrCH2COOEt CH3IA TM86.OHON2cr03+CH3CH2MgBrH3O87.12 EtONa 廣 Na OH _2Br(CH2)5Br HCl .Et2OCOOHCH2cH30H88.CH3IEtONa Cl-CHCOOC2H5Na OHH3O+EtOHCH3CCH2CHCOOHO CH3H2SO4NBSH2OBr295.CH2=CHCH2CH3NBSNaOH忑TM1CH3cH2MgX尸HSO4 B2H6CH2CH32H2O/ H+ A H2O2/OH -OOH1CH3CH2MgX. HSO4 - HBr / H2O2尸2H20 / H+ NaOH小20