《有机化学》课件-第四章炔烃二烯烃.ppt.ppt

1、l CCRRCCRRCCHRH2CCHCH2CH2CHCHCH2CCHCH2CHCH2CCH12345678912345678912345HCH3CH2烷烃碳烷烃碳: sp3杂化杂化烯烃碳烯烃碳: sp2杂化杂化炔烃碳炔烃碳: sp杂化杂化 CH3-甲基负离子甲基负离子CH2=CH-乙烯基负离子乙烯基负离子CHC-乙炔基负离子乙炔基负离子稳定性稳定性碱性碱性Pt,Pd或或NiH2Pt,Pd或或NiH2乙烯和乙炔的电离势能乙烯和乙炔的电离势能(1015和和1088kJ/mol)也说明了这点也说明了这点.烯基碳正离子的结构烯基碳正离子的结构sp2杂化杂化sp杂化杂化 + 2个个p轨道轨道HgCl2

2、或或Cu2Cl2H2SO4HgSO4分子重排分子重排H2SO4HgSO4分子重排分子重排烯醇式化合物烯醇式化合物 酮酮记住反应记住反应条件！条件！CHCH + HCNH2CCHCNCuClNH4ClCu2Cl3+NH4ClH2O+ CH CH催化剂催化剂Ni(CN)2,(C6H6)3P醚醚苯苯Ni(CN)2醚醚环辛四烯环辛四烯20001500 0.010.1sHClHOHCH3OHHCNCH3COOH注意：中间注意：中间C为为sp杂化杂化 CH2=C=CH2sp2sp(1)每个碳原子均为每个碳原子均为sp2杂化的杂化的.(2)四个碳原子与六四个碳原子与六个氢原子处于同一个氢原子处于同一平面平面

3、.键所在平面与纸面垂直键所在平面与纸面垂直键所在平面在纸面上键所在平面在纸面上CH2CCCH2HHS-顺式丁二烯CH2CCHHCH2S-反式丁二烯ENuCHCHH2CCH2CHCHH2CCH2123CHCHH2CCH2CHCHH2CCH2CHCHH2CCH245NuENuEENuCHCHH2CCH2BrHCHCHH2CCH2HBrCHCHH2CCH2HBr（无无过过氧氧化化物物）+注意：双键位置有变化注意：双键位置有变化CHCHH2CCH2HBrCHCHH2CCH2HCHCHH2CCH2HBrBrCHCHH2CCH2BrHCHCHCH2H2CHBrCHCHH2CCH2HBrCHCH2CH2CH

4、2HBrCHCHH2CCH2BrHCHCHH2CCH2HBr CHCHH2CCH2HBr+CHCHH2CCH3BrCHCHH3CCH2BrCHCHH2CCH3CHCHH2CCH3CHCH2CH2CH3势势能能反反应应进进程程Br+CHCHH2CCH2ClCHCHH2CCH2ClCHCHH2CCH2HCl 20oC7580%75%25%2520%+HHCHCHH2CCH2ClCHCHH2CCH2ClCHCHH2CCH2Cl2+ClCl 200oC67%70%30%33%CHCHCHCHHClCH3CH3CHCHCHCH CH3CH3HClCHCHCHCHClHCH3CH3+2-氯氯-1,3-丁二烯丁二烯2-甲基甲基-1,3-丁二烯丁二烯(异戊二烯异戊二烯)是沸点为是沸点为34的液体。的液体。天然橡胶杜仲胶