有机化学课后习题答案 南开大学 醇和酚.docx

《有机化学课后习题答案 南开大学 醇和酚.docx》由会员分享，可在线阅读，更多相关《有机化学课后习题答案 南开大学 醇和酚.docx（26页珍藏版）》请在三一办公上搜索。

1、有机化学课后习题答案 南开大学 醇和酚第九章 醇和酚 1. 命名下列化合物： 2-乙基-1-己醇 3-甲基-2-丁烯醇 溴代对苯二酚 5-氯-7-溴-2-萘酚 -4-甲基-5-苯基-1-戊烯-3-醇 2. 完成下列反应式： CH2OHClCH3(1)Cl(2)(3)HOCH2CH3CH3(4)(5)CH3OH(6)OO CH3CH3(7)HBrIHHIBrH(8)CCOCH3CH2CH3CHO2CH3OCH33. 用化学方法将下列混合物分离成单一组分。 OH水层H+苯酚(1)NaOHOHH2O油层环己醇OHO2NNO2水层H+2，4，6-三硝基苯酚(2)NO2NaHCO3CHH2O3O2NNO

2、油层2，4，6-三硝基甲苯2NO24. 用简单的化学方法鉴别下列化合物。 先用FeCl3检验出苯酚，用Na检出溴苯，然后用Lucas试剂检验出伯、仲、叔醇。5. 按与氢溴酸反应的活性顺序排列以下化合物。 6. 按亲核性强弱排列下列负离子： 1 OHCOHOH7.CC2H5H+O+C2H5H+C2H5C2H5C2H5OH+C2H5H2OCC2H5H+C2H5OHOHCC6H5H+H2OOCC2H5C2H5OOHC+C6H5H+C6H5C6H5C6H5C6H58. 写出下列反应可能的机理： OH(1)CC2H5H+H2O+C+C2H5H+C2H5C2H5C2H5C2H5C2H5+C2H5H+C2H

3、5C2H5OH(2)H+H2O+H+(3)C2H5CHCH3OHH+H2OC2H5CHCH3+C2H5CH3H+C2H5CH3OHOH(4)H+H2O+OHH+OH+O+NaBH4H+H2OOH+ 2 (5)CH3OOHH+CH3OCH3OH+CH3O+CH3OOH9. ACH3或OHCH3DCH3或OHCHCH3BOCH3或CH3ECH3或OCCH3OHCCH3CH3CCH3CH3OHFHOCH3CH3或OHOHCH3CH3HOCCH3CH310. 完成下列转化： (1)CH2OHH2SO4Br2BrNaOH醇(2)HOCH3H2SO4B2H6H2O2OH-CH3C2H5ONaOH及对映体H

4、HCH3TsClOTsHHCH3醇CH3OCH3CCH2CH3CH3H2OH+(3)OHPBr3Mg乙醚MgBrCOHCH2CH3(4)(CH3)2NB2H6H2O2OH-SarrettCrO3.Py(CH3)2NOH(CH3)2NO11. 以苯、甲苯、环己醇及四个碳以下的有机物为原料合成： 3 (1)Br2FeBrMg乙醚OMgBrH2OH+HOH2SO4Cl(2)CH3CH2ClAlCl3CH2CH3Cl2hvCCH3ClOCCH3C2H5ONa醇CCHC2H5MgBrCH3H2OH+CCMgBrCCCOHO2NHNO3(3)CH3H2SO4HO3SCH3NaOH熔融OHOCH3HOCH3

5、HOCH3(4)CH3Br2FeMg乙醚CH3MgBrH2OH+HOH2SO4CH3B2H6H2O2OH-CH3(5)(CH3)3CClMg乙醚(CH3)3CMgClClCH2CH=CH2(CH3)3CCH2CH=CH2CH3CH3CCH2CH2CH3CH3H2SO4H2Ni(6)OHN2CrO3OCH3MgBrH2OH+OHCH3CH3CH3CH3B2H6H2O2OH-OHK2Cr2O7H2SO4OOCH3CCH3OHH2OH+(7)CH3CH2CH2CH2BrPBr3Mg乙醚CH3CH2CH2CH2MgBrBrCH3CH2CH2CH2CCH3CH3CH3CH2CH2CH2CCH3CH3CH

6、3CH2CHCH2OHCH3PBr3(8)CH3CH2CHCH3BrNaOH醇Mg乙醚HCHOH2OH+CH3CH2CHCH2BrCH3CH3CH2C=CH2CH3 4 (9)CH3CH2ClAlCl3CH2CH3H2SO4HO3SBrCH2CH3NaOH熔融HOCH2CH3NBSHOCHCH3NaOH醇NaOCH=CH2CH2ClCH2OCH=CH2(10)H2SO4HO3SNaOH熔融HOCH3IOH-CH3OBr2FeOHCH3OBrMg乙醚CH3OMgBrCH3CHOH2OH+CH3OCHCH3OOOH12.ABCOTs13.(CH3)3COTs(CH3)3CHHC2H5ONaE2(C

7、H3)3C及对映体 按E2反应机理反应，所以速率与对甲苯磺酸酯、乙氧基负离子浓度均成正比。 H(CH3)3C(CH3)3COTsHOTsC2H5ONaE1(CH3)3C及对映体 因稳定构象很难翻转，OTs不能处于直立键，无法反式共平面消除，所以只能按E1机理反应，故反应速度慢，且反应速率只取决于对甲苯磺酸酯的浓度。 CH314.AOHCH3DOHCH3ECH3或OHCH3FHOCH3CH3CH3BOHOHCH3COCH3Cl15.ClOHHBr, SN2( + )构型转化Br( + ) 5 ClHBr, 邻基参与构型保持Cl当卤素与羟基处于顺式时，卤素不能发生邻基参与，只能发生SN2反应，构型

8、发生翻转，生成反式的卤代物，当卤素与羟基处于反式时可以邻基参与，构型保持，因而生成相同的产物。 OHH3CCH3OH+CH3H16.CH3CHOCH3OCH3HOOHCH3HOCH3H+OH( + )Br( + )CH3CH3O 重排为反式共平面重排，且发生在环上的反应，a键反应活性比e键高。 17. 发生了溴的邻基参与反应。 BrCH3HS, RCCCH3HOHH+BrCH3HCC+CH3HOH2BrCH3H+CCCH3HBr-BrCH3CHCH3CHBrS, RCH3BrHCCH3CCH3HOHH+BrHCH3CC+CH3HOH2BrHCH3+CCCH3HBr-BrHCH3R, RCCHBrR, R它们对映体的生成过程类似。 CH318.CH3CCH2OHH+CH3CH3CCH2OH2+CH3CH3CCH2+CH2OHCH3C+CH2OHCH3+CH2OHCH3H+CH2CH3HCHOH19. A； C； E； B； D. CH3CH2CHCH=OHCH3CH2CHCHO 6