厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十七章 酚Phenols 17.2.2 芳环上的反应

1722芳环上的反应 OH 室温Br Br t Bro/h,o Br OH OH Br Br t Bro/h,o SORE Br

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 17.2.2 芳 环上的反应 OH + Br 2/H 2 O 室温 OH Br Br Br 白 OH + Br 2/H 2 O OH Br Br Br 白 SO 3 H

OH OH CS. 2 t br t hBr Br OH HOAC Br t Br 回流 Br

Organic Chemistry Organic Chemistry Xiamen Xiamen University University OH + Br2 OH CS 2 5 Br + HBr OH + Br2 OH Br HOAc 回流 OH Br +

OH 10~25 SO3H 98%H2SO4 100 OH 100 OH SO3H ①D 98%H,SO SO,H 100 ⑨D SO3H

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10~ 2 5 OH 98% H 2SO 4 100 OH SO 3 H OH SO 3 H 100 98% H 2SO 4 100 OH SO 3 H SO 3 H

OH OH OH 20%HNO NO 25 NO2 15 30~40 OH NO 浓HNO3 浓HNO9 nO. ①D NO ⑨D NO

Organic Chemistry Organic Chemistry Xiamen Xiamen University University OH 20% HNO 3 25 OH NO 2 OH NO 2 + 15% 30~40% OH NO 2 NO 2 浓HNO 3 浓HNO 3 OH NO 2 O 2 N NO 2

OH OH (CH33C H2SO4 C(CH3)3 + CH3)2C=CH2 △ CHa CH OH BE ①D Chr,H (主) ⑨D C-CH 3

Organic Chemistry Organic Chemistry Xiamen Xiamen University University OH CH 3 (C H 3 ) + 2C C H 2 H 2SO 4 OH CH 3 C(CH 3 ) 3 (C H 3 ) 3 C OH CH 3CO 2 H B F 3 OH C C H 3 O + ( 主 )

OH HO OH HoSO 4 酚酞 O HO O O OH ①D HSO. CO,H ⑨D OH O 荧光黄

Organic Chemistry Organic Chemistry Xiamen Xiamen University University OH O O O + H 2SO 4 酚酞 O C O OH HO OH O O O + H 2SO 4 OH HO O O CO 2 H 荧光黄

gpH>9时酚酞转变为粉红色的酚酞负离子: HO OH O 2OH C C O 酚酞 酚酞负离子 O无色 O粉红色 OH ①D C ⑨D 酚酞负离子 粉红色

Organic Chemistry Organic Chemistry Xiamen Xiamen University University pH >9 时酚酞转变为粉红色的酚酞负离子 酚酞 C O O C O C O OH HO O O 无色 酚酞负离子 粉红色 2OH C O OH C O O 酚酞负离子 粉红色

己缩合反应OH HoSO CH3-C-CH CH HO- OH CH 双酚A 司反应机理 Bisphenol a OH OH DCH3C-CH3-CH3-C-CH3--CH3C-CH3

Organic Chemistry Organic Chemistry Xiamen Xiamen University University OH 2 + H 2SO 4 CH3 C C H3 O HO C OH CH3 CH3 双酚A B isphenol A CH 3 C C H 3 O CH 3 C C H 3 O H CH 3 C C H 3 O H H + 反应机理 缩合反应

390 H CH CH2C-Ch +HO HO C-OH -H CH CH3 CH H OH ●Ho《C-OH HO C+ HO CH CH CH CH OH/O OH H+ HO OH CH CH ⑨D

Organic Chemistry Organic Chemistry Xiamen Xiamen University University CH 3 C C H 3 O H + HO HO C CH 3 CH 3 OH H HO C CH 3 CH 3 OH H + H 2 O HO C CH 3 CH 3 OH HO C CH 3 CH 3 OH − H + H − H + HO C CH 3 CH 3 OH

CHoCI HO C|C|C OH Naoh CH Ho- > 2 CH CH - Eho C OCH2 环氧树脂

Organic Chemistry Organic Chemistry Xiamen Xiamen University University HO C CH 3 CH 3 OH O CH 2Cl NaOH HO C CH 3 CH 3 OCH 2 O CH 2 O C CH 3 CH 3 OCH 2 O O 环氧树脂