第十一章醚 chapter 11 ethers 1、写出下列化合物的名称 答 已基环己基醚 答 已基仲丁基醚 OH 乙氧基乙醇 OCH3 对硝基苯甲醚 2、写出下列反应的产物。 (1)(CH3)3CCH2OCH3+HBr -CH3Br+(CH3)CBrCH2CH3 (2)S-C4HoOCAHo-t+HI- t'c4Hgl+ S-C4HgOH H, Pd/c (3) CH3O- CH,,CH3 CHO CH3+ CH3 CH,OH H2 Pd/C 6Hs( CH2)4CHOH C6H5 3、写出下列化合物的克莱森重排产物 OCH2CH=CH2 CH2CH=CH
第十一章 醚 chapter 11 ethers 1、 写出下列化合物的名称。 (1) O 答: 已基环己基醚 (2) O 答: 已基仲丁基醚 (3) O OH 答: 2—乙氧基乙醇 O OCH3 (4) 2N 答: 对硝基苯甲醚 2、写出下列反应的产物。 (CH3 ) (1) 3CCH2OCH3+HBr CH3Br+(CH3 )2CBrCH2CH3 (2) s-C4H9OC4H9 _ t+HI t -C4H9 I+ s-C4H9OH (3) CH CH2OCH2CH3 3O H2 Pd/C CH3O CH3 + CH3CH2OH (4) O C6H5 H2 Pd/C C6H5 (CH2 )4CH2OH 3、写出下列化合物的克莱森重排产物。 CL OCH2CH=CH2 CL (1) HO HO CH2CH=CH2 OH
3C OCH2C=CH2 H3 CH2C=CH2 H3CO OCH3 H2C=HCO CH2CHO 4、写出下列反应的产物 CH,ONa (CH3)CH一cHCH3 (CH3hC CHeCH OH OCH3 CH3 OH -OH H3C CH2OH CH2 +H,O-H, (H3C)3C C(H3C)3 OH (4 CH2 +H,OOH (H3C)3C CH2OH (1)(CH3 )2Cu Li C2Hs CHOHC2H5 ChICH
H3C OCH2 (2) HO OH H2C (3) H3CO OCH2C=CH2 CH3 H H3CO CH2C=CH2 OCH3 OH CH3 (4) H2C=HCO CH3 CH3 CH2CHO 4、 写出下列反应的产物。 (1) (CH3 )2C CH2CH3 O + CH3ONa (CH3)CH OH CHCH3 OCH3 (2) O H3C + OH - CH3 OH OH (3) (H3C)3C O CH2 +H2O H + C(H3C)3 CH2OH OH (4) (H3C)3C O CH2 +H2O OH - C(H3C)3 OH CH2OH (5) C2H5CH O (1) (CH3)2Cu + Li - H + C2H5CHOHC2H5 2
HO naCN OCHCHOCN (7) nCBC≡c+ (1)Et20 nC4HC≡ CMgCH2CH2OH (2)H3O 5、推测下列反应的机理。 (CH3)COK OH CH3 H3CHC—C OC(CH3)3-- H2C=CHC(CH3)2 H3 CHCC=CH2 H2 (CH3)3COH 2HC-CHC(CH3)2+ H3CHCC-CH2 (CH3)3CO CH3 (2)HOCCH=CH HOBr C(H3C)2--CHCH2Br CH3 ABr coh HOCCH-=CH CH3CH-H—cH2 H2Br (H3C)3C CH2 Br 6、写出下列化合物如何合成 (1)(CH3)3COC(CH3)3(对酸性试剂非常敏感) D)Hg(oAch ( CH3)2C-CH2 +(CH3)3COH CH3)3COC(CH3)3 2)NaBH
3 (6) O + NaCN H2O HOCH2CH2CN 4 (7) n-C4H9C CMg + O (1)Et2O (2)H3O + n-C4H9C CMgCH2CH2OH 5、推测下列反应的机理。 5 (1) O H3CHC C(CH3 )2 (CH3 )2CO -K + (CH3 )2COH H2C C H C(CH3 )2 OH +CH2CHOHC CH2 CH3 O H3CHC C CH3 C H2 H -OC(CH3 )3 H2C CHC(CH3 )2 O - + H3CHCC CH2 -O CH3 (CH3 )3COH -(CH3 )3CO - 2HC CHC(CH3 )2 OH + H3CHCC CH2 CH3 HO (2) HOCCH CH2 CH3 CH3 + HOBr O C(H3C)2 CHCH2Br HOCCH CH3 CH3 CH2 Br OH CH3CH H:O: CH3 HC Br CH2 H O+ CH2Br H3C H3C H + O (H3C)3C CH2Br 6、写出下列化合物如何合成。 (1)(CH3)3COC(CH3)3 (对酸性试剂非常敏感) (CH3 )2C CH2 + (CH3 )3COH 1) Hg(OAc)2 2) NaBH4 CH3 )3COC(CH3 )3 6
H3)2COCH,OC CH3 CO3H CH3O (H3C)2HC (CH3) CHCHOHCH,OCH3 氧化 (CH3)CHCOCH2OCH3 CH2CH= CH2 NO H2SO4 OCH2 CH=CH2 NAoH CH2CH=CH2 2)CH,=CHCH,CI 7、推测下列化合物的结构 (1)Cn2H1g,δH:1.2(t,6H,3.4(q,4H),4.4(s,4H),用高锰酸钾氧化 生成对苯二甲酸 2)C6H14O,δH:1.2(d 答案 (1) CH2OCH2 CH3 (CH3)CHOCH(CH3h CH2OCH2 CH3
(2) (CH3 )2COCH2OCH3 CH3CO3H O (H3C)2HC CH3O - (CH3 )2CHCHOHCH2OCH3 氧化 (CH3 )2CHCOCH2OCH3 (3) OH LC CH2CH NO2 CH2 3) H2SO4 SO3H NaOH H2SO4 Fe Cl2 NO2 OH NO2 Cl 1)NaOH 2)CH2=CHCH2Cl OCH2CH=CH2 NO2 Cl OH NO2 Cl CH2CH=CH2 7、推测下列化合物的结构 (1) C12H18,δH: 1.2(t ,6H),3.4(q ,4H),4.4(s ,4H),用高锰酸钾氧化 生成对苯二甲酸。 (2) C6H14O, δH: 1.2(d ,12H),3.6(m ,2H)。 CH2OCH2CH3 CH2OCH2CH3 答案: (1) (CH3 )2CHOCH(CH3 )2 (2)