大学有机化学反应方程式总结(较全).pdf
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1、有机化学一、烯烃1、卤化氢加成(1)CHCH2RHXCHCH3RX【马氏规则】在不对称烯烃加成中,氢总是加在含碳较多的碳上。【机理】CH2CH3CH+CH3CH3X+CH3CH3X+H+CH2+CH3X+CH3X主次快慢【本质】不对称烯烃的亲电加成总是生成较稳定的碳正离子中间体。【注】碳正离子的重排(2)CHCH2RCH2CH2RBrHBrROOR【特点】反马氏规则【机理】自由基机理(略)【注】过氧化物效应仅限于HBr、对 HCl、HI 无效。【本质】不对称烯烃加成时生成稳定的自由基中间体。【例】CH2CH3HBrBrH+CHCH2BrCH3CH+CH3CH3HBrBrCH3CH2CH2BrC
2、HBrCH3CH32、硼氢化 氧化CHCH2RCH2CH2ROH1)B2H62)H2O2/OH-【特点】不对称烯烃经硼氢化氧化得一 反马氏加成 的醇,加成是 顺式 的,并且不 重排。【机理】CHCH2CH3CHCH3CH3BH2HCHCH3CH3BH2HCH CH2CH3HBH2CH3CH=CH2(CH3CH2CH2)3BO-OHOHB-OH3CH2CH2CCH2CH2CH3CH2CH2CH3BOCH2CH2CH3H3CH2CH2CCH2CH2CH3+OH-OHO-B-OCH2CH2CH3CH2CH2CH3H3CH2CH2COOHBOCH2CH2CH3CH2CH2CH3OCH2CH2CH3HO
3、O-B(OCH2CH2CH3)3B(OCH2CH2CH3)3+3NaOH 3NaOH3HOCH2CH2CH33+Na3BO3BH2H【例】CH31)BH32)H2O2/OH-CH3HHOH3、X2加成CCBr2/CCl4CCBrBr【机理】CCBrBrC+CBrCCBr+Br-CCBrBrCCBr+OH2CCBrOH2+-H+CCBrOH文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP
4、9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6
5、N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F
6、10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:
7、CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 H
8、W6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM
9、1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编
10、码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5【注】通过机理可以看出,反应先形成三元环的溴鎓正离子,然后亲和试剂进攻从背面进攻,不难看出是反式加成。不对称的烯烃,亲核试剂进攻主要取决于空间效应。【特点】反式加成4、烯烃的氧化1)稀冷高锰酸钾氧化成邻二醇。CH3CH3CH3CH3稀 冷 KMnO4CH3CH3CH3CH3MnOOOOH2OCH3CH3CH3CH3OH OH-2)热浓酸性高锰酸钾氧化CCHRR2R1KMnO4H+CRR1O+R2COHO3)臭氧氧化CCHRR2R1CRR1O+R2CHO1)O32)Zn/H2O4)过氧酸氧化CCHRR2R1ROOOHOR
11、HR2R1CCHRR2R1ORHR2R1Ag+O25、烯烃的复分解反应nCH2RCH2R1+催化剂CH2CH2RR1【例】文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F1
12、0Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:C
13、P9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW
14、6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1
15、F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码
16、:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5
17、HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5OCH2CH2C6H5Grubbs catalystOC6H5+CH2CH26、共轭二烯烃1)卤化氢加成CH2CH2HXHXCH3XCH2CH
18、3X高温1,4加成为主低温1,2加成为主2)狄尔斯-阿德尔(Diels-Alder)反应【描述】共轭二烯烃和烯烃在加热的条件下很容易生成环状的1,4 加成产物。【例】CH2CH2+OOO苯OOOCH2CH2+苯CHOCH2CHO二、脂环烃1、环丙烷的化学反应【描述】三元环由于张力而不稳定,易发生加成反应开环,类似碳碳双键。H2/NiBr2/CCl4H2SO4HX(X=Br,I)CH2CH2CH2HHCH2CH2CH2BrBrCH2CH2CH2HOHCH2CH2CH2HX【特点】环烷烃都有抗氧化性,可用于区分不饱和化合物。【注】遵循马氏规则【例】文档编码:CP9V7J2O6X5 HW6N8U3J
19、6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L
20、7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7
21、J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U
22、3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q
23、4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9
24、V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N
25、8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5文档编码:CP9V7J2O6X5 HW6N8U3J6X6 ZM1F10Q4L7T5CH3HBrCH2CHCH2HBrCH32、环烷烃制备1)武兹(Wurtz)反应【描述】通过碱金属脱去卤素,制备环烷烃。【例】CCXXZnC2H5OHCCCH2XCH2XZnNaI双键的保护BrBrK2)卡宾卡宾的生成A、多卤代物的消除X3CH+Y-NaOH,RONa,R-LiCXX+X-+HYB、由某些双键化合
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