ORGANIC CHEMISTRY Chapter 8 8.5 Addition of water to alkenes Acid-Catalyzed Hydration 烯烃与水的加成:酸催化水合反应 Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 8.5 Addition of Water to Alkenes: Acid-Catalyzed Hydration 烯烃与水的加成 酸催化水合反应
ORGANIC CHEMISTRY Chapter 8 OH HO C=C、+H-OH H H3 PO4 CH2=CH2+ H2O CH3,OH 300,70atm H3O (CH3)2C=CH2 H2O 25°C(CH3)2COH Mechanism H2O (CH3h2C=CH2 (CH3)3C20 (CH3)3C-OH HO CH33C-OH H Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 C C + H OH H3O C C H OH CH2 CH2 + H2O 300 , 70 atm CH3CH2OH H3PO4 (CH3)2C CH2 + H2O H3O 25°C (CH3)3COH Mechanism (CH3)2C CH2 H3O (CH3)3C H2O (CH3)3C OH2 H2O H (CH3)3C OH
ORGANIC CHEMISTRY Chapter 8 One complication associated with alkene hydration is the occurrence of arrangements CH HoSO OH CH3 CH3-C-CH=CH H0 CH3-C-CH-CH3 CH CH The carbocation formed initially invariably rearrangement to a more stable one if such a rearrangement is possible CH3 CH3 Y H CH3-C-CH-CH CH -C-CH-Ch-Q CH CH H Y CH OH CH H2O CH3-C-CH-CH2 CH3C—CH-CH H CH3 H CH Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 One complication associated with alkene hydration is the occurrence of arrangements C CH CH2 CH3 CH3 CH3 H2SO4 H2O C CH CH3 CH3 OH CH3 CH3 The carbocation formed initially invariably rearrangement to a more stable one if such a rearrangement is possible. C CH CH2 CH3 CH3 CH3 C CH CH2 CH3 CH3 CH3 H C CH CH2 CH3 CH3 H CH3 H+ H2O C CH CH3 CH3 OH CH3 CH3 H
ORGANIC CHEMISTRY Chapter 8 Oxymercuration- demercuration(羟汞化-脱汞反应) 1)Hg(OAc)2, H2O CH CH (2)NabH4 OH92% OAc OAc Hg-oac Hg-oac HoO CH3 CH H Aco H Hg-oac CH3 NabH4 CH3 OH OH AcOH Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 Oxymercuration-demercuration(羟汞化-脱汞反应) CH3 (1) Hg(OAc)2, H2O (2) NaBH4 CH3 OH 92% CH3 CH3 OH Hg OAc OAc CH3 Hg H2O CH3 Hg OAc O H H CH3 Hg OAc OH AcO AcOH NaBH4 OAc
ORGANIC CHEMISTRY Chapter 8 Hydroboration- oxidation(硼氢化一氧化反应) BRCH=CH2 B2H6 (RCH2CH2)3B Hydroboration H,O2 (RCH2 CH2)3B BRCHCHOH OH Oxidation B(OH)3 2BH B2H6 B B Borane Diborane H 甲硼烷 乙硼烷 H Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 Hydroboration–oxidation (硼氢化 氧化反应) 3RCH CH2 + B2H6 3RCH2CH2OH + B(OH)3 (RCH2CH2)3B (RCH2CH2)3B H2O2 OH Oxidation Hydroboration H B H H H B H H 甲硼烷 乙硼烷 2BH3 B2H6 Borane Diborane