第11章芳香烃的化学性质 11-1 (④CH人CH,CHCH, mam2。m -COOCH .CH 0→④-⑤m,-④-cl,-Q0, 13④G+1P-cc1
1 11 11-1 11-2 ✁✂☎✄ ✆✞✝ ✟ ✠☛✡ ☞ ✡ ✌ ✡ ✟✎✍ H CH3 CH3 Br Br Br C(CH CH2CH2CH3 3)3 CH3 CH3 OCH3 CH NO2 3 CH3 NO2 Cl NO2 NO2 NHCOCH3 COOCH3 CH3
CH3 OH 18 C00H 11-3 CH3 -CH,cH,2CH,-○ ,G-O⊙-c00H H 5c1cH一⊙-cH,60 NO2 oC大◇-CH-CHCHCH:rO-CHCH.CH 12:CH:0②。分CH,0-⊙CHCH,④ Br 13·G-CH2CH,G-CHCH3⑤-CHS
2 ✏ ✑✓✒ ✑✕✔ ✏ ✑✕✖ ✗ ✘✚✙ ✘✚✛ 11-3 ✜ ✜ ✜ ✢ ✣ ✜ ✣ ✤ ✥ ✥ ✦ ✧ C C CH3 H H ★ ★ ✩ ✪ ★ ✫ 11 . 10 . CHCH2CH3 Cl CH=CHCH(CH3 )2 NO2 CH3 NO2 ✬ ✭ ✮ O O
Br 14H0S@-CH3H0S-令-CH3 "a, Br Br 15. CH30CHCH3 CH30CHCHs O2N、 CH,0OCH②CH,0-OCHO CH 16.CrO3/CH3COOH 0 0 Oc-a②c0 NO2 NO2 19⊙-C-0-⊙N022”0N@⑦- 21.PhCHCHCH-CH2 Br Br 11-4 1ON○CH2G-CF32不反应 3C0CH4不反应
3 CH2CH3 CHCH3 Cl 15 . CH3O CH3O CH CH3 CH CH3 O2N CH3O CH3O 16 . CrO3 /CH3COOH 17. O O NO2 18 . Cl O C NO2 NO2 O C 19. C 20. O O NO2 O2N CF3 21. PhCHCHCH CH2 Br Br = 11-4 COCH3 O2N CH2 CF3 1 . 2 . 3 . 4.
11-5 CHs 褪色 KMnO4/H' O Br2/H2O X O KMnO/H' 褪色 褪色 △ CHs 褪色 11-6 1.A>B>D>C 2.B>A>C 3.A>C>B 4.A>B 5.C>B>A 6.(i)A>D>B>C (2)B>C>A (3)C>B>D>A 11-7 具有芳香性的化合物有：1,58,10,11,12. 11-8 O2N NO2 NO2 NO2 NO NO2 11-9 0 11-10 卓酮是具有芳香性的环酮，芳环具有较大的稳定性，容易发生亲电取代反应 11-11 甲迁修 一
4 11-5 CH3 CH3 Br2 /H2O KMnO4/H + KMnO4/H + 11-6 1 . A>B>D>C 2 . B>A>C 3 . A>C>B 4 . A>B 5 . C>B>A 6 . (1 ) A>D>B>C (2 ) B>C>A (3 ) C>B>D>A 11-7 :1,5,8,10,11,12. 11-8 O2N NO2 NO2 NO2 + + NO2 NO2 NO2 NO2 11-9 COOH CH3 O O 11-10 , ,. 11-11 OH H + O +H2 -H2O + ✯✱✰✳✲✳✴ 1. + H + -H +
CHCHCH.CH-CHCH,CH.CHCH.HCH.CH CH-CH3 H CH2CH3 CH3 H CH3 CHs CHs c出QcH二，产物 H CH3 11-12 CH3 CH3 CH3 1 心Br所S霸 △ SOH SO:H CH3 CH3 CH3 2. Br/Fe HNO:/H2SO4 NO. ,1y,产物 (去除邻位产物 Br Br Bo/Fe Br-Br CH2CH3 CH=CH2 4 Br:/Fe A1C13
5 2. CH2CHCH2CH=CHCH3 H + CH2CHCH2CHCH2CH3 CH3 3. C=CH2 C CH3 H + CH3 C=CH2 CH3 CH3 C CH2 C CH3 CH3 CH3 CH3 CH3 H CH3 H + 11-12 CH3 CH3 SO3H 1. H2SO4 Br2 /Fe CH3 Br Br SO3H H+,H2O 2. CH3 Br NO2 CH3 Br2 /Fe Br CH3 (✵✳✶✸✷✺✹✼✻✺✽) HNO3 /H2SO4 Cl2 / hγ 3. Br2 /Fe Br HNO3 /H2SO4 NO2 Br Br2 /Fe NO2 Br Br Br CH2CH3 4. Br2 CH /Fe 3CH2Cl AlCl3 -H2 Cat. CH=CH2 CH2CH3 H CH2CH3 + H +
CHBrCH2Br CCH ⊙ 2B, CI SO3H 。⊙cH,,②-CH.CM/F醚， CHAMgCI D:0CH.D CH3 00H NO2 NO. CH3 CH3 CH3 IN0 SO.NO: COCH3 COCH ,2⊙+CCH,CH=CHCH,QAC产物 0 11-13 BGC⊙oa CH3 EO
6 CHBrCH2Br C CH - HBr 2 6 . CH CH2Cl 3 Cl2 / hγ Mg / ✾❀✿ CH CH2D 2MgCl D2 O 8 . CH3 CH3 COCH3 CH3COCl / AlCl3 HNO3 /H2SO4 CH3 COCH3 NO2 9. 2 + ClCH2CH=CHCH2Cl AlCl3 10. CH3 CH3 O O O / AlCl3 O HO O H CH3 PPA / --H2O O O 11-13 CH3 C CH CH3 CH2CH3 COOH B C COOH A CH3 C C D O O O E HNO3 /H2SO4 Cl SO3H NO2 Cl SO3H Cl H2SO4 2 / Fe Cl 5 . COOH NO2 Br CH3 NO2 Br Br2 /Fe CH3 NO2 HNO3 /H2SO4 CH3 7 . KMnO4