中因石油大学 CHINA UNIVERSITY OF PETROLEUM 不对称醚醚键的开裂取向 CH3 HI CH3 CH 31 H H △ CH3-l CH3 小 2°大 CH3 CH3 HI CH3 CH3 CH3 CH3OH + I-C-CH3 △ CH3 CH3 小 3°很大 如何解释以上反应取向？ 12143
12/43 不对称醚醚键的开裂取向 小 小 大 很大 如何解释以上反应取向？ 2 o 3 o CH3CH2 O CH2CH2CH3 CH3CH2 OH + I CH2CH2CH3 CH3CH2 I + HO CH2CH2CH3 HI CH3 O CH2CH2CH3 HI CH3 I + HO CH2CH2CH3 CH3 O C CH3 CH3 HI CH3 OH + CH3 O CH3 CH3 H HI CH3 I + HO CH3 CH3 H CH3 I C CH3 CH3 CH3 CH3CH2 O CH2CH2CH3 CH3CH2 OH + I CH2CH2CH3 CH3CH2 I + HO CH2CH2CH3 HI CH3 O CH2CH2CH3 HI CH3 I + HO CH2CH2CH3 CH3 O C CH3 CH3 HI CH3 OH + CH3 O CH3 CH3 H HI CH3 I + HO CH3 CH3 H CH3 I C CH3 CH3 CH3 CH3CH2 O CH2CH2CH3 CH3CH2 OH + I CH2CH2CH3 CH3CH2 I + HO CH2CH2CH3 HI CH3 O CH2CH2CH3 HI CH3 I + HO CH2CH2CH3 CH3 O C CH3 CH3 HI CH3 OH + CH3 O CH3 CH3 H HI CH3 I + HO CH3 CH3 H CH3 I C CH3 CH3 CH3 CH3CH2 O CH2CH2CH3 CH3CH2 OH + I CH2CH2CH3 CH3CH2 I + HO CH2CH2CH3 HI CH3 O CH2CH2CH3 HI CH3 I + HO CH2CH2CH3 CH3 O C CH3 CH3 HI CH3 OH + CH3 O CH3 CH3 H HI CH3 I + HO CH3 CH3 H CH3 I C CH3 CH3 CH3
中因石油大学 CHINA UNIVERSITY OF PETROLEUM 瞇键开裂机理（亲核取代反应机理 ·S、2机理 CH3 CH3 CH3-O H CH3 -H CH3 H CH3 SN CH3 CH3—I+ HO- 一H CH3 S2,位阻影响为主 13/43
13/43 I H CH3 O CH3 CH3 H CH3 O CH3 CH3 H H I CH3 I + HO CH3 CH3 H 醚键开裂机理（亲核取代反应机理） • SN2 机理 SN2 SN2，位阻影响为主 I H CH3 O CH3 CH3 H CH3 O CH3 CH3 H H I CH3 I + HO CH3 CH3 H
中因石油大学 CHINA UNIVERSITY OF PETROLEUM Sx1机理 CH3 CH3 CH3- ● C一CH3 CH3 CH3 CH3-OH Sy! S、1,中间体稳 CH3 定性为主 C-CH3 CH3 CH3 -CH3 CH3 14/43
14/43 I C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 H I CH3 OH + C CH3 CH3 CH3 I I H • SN1 机理 SN1，中间体稳 定性为主 I C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 H I CH3 OH + C CH3 CH3 CH3 I I H SN1 I C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 H I CH3 OH + C CH3 CH3 CH3 I I H
中因石油大学 CHINA UNIVERSITY OF PETROLEUM ■ 芳基烷基醚的开裂取向 脂肪烃基C-O键断裂！ OH C2Hsl + HI 不反应 15/43
15/43 芳基烷基醚的开裂取向 脂肪烃基C-O键断裂！ O-C2 H5 OH + HI C2H5I + O HI 不反应