10.5 Alcohols from alkenes through oxymercuration Demercuration (1) Hg(oAc)2/THF H2O Oxymercuration OH HgOCoCH3 (2)NaBH4/H2o Demercuration(脱Hg OH H
10.5 Alcohols from alkenes through oxymercurationDemercuration + H2O ( 1 ) Hg(OAc) 2 / THF OH HgOCOCH3 Oxymercuration ( 2 ) NaBH4 / H2 O OH H Demercuration (脱 Hg)
(1) Hg(oach/THF CH3(CH2)2CH=CH2 +H2O CH3(CH2)2Hc—cH Oxymercuration OH HgOCOCH3 (2)NaBH4/H2O CH3(CH2)2 CHCH2 Demercuration(脱Hg) OH H CH CH3 (1) Hg(OAch/THF +H2O一 OH (2)NaBH4/H2o H 1-Methylcvclohexanol
H2O ( 1 ) Hg(OAc) 2 / THF ( 2 ) NaBH4 / H2O + CH3 CH3 OH H 1-Methylcyclohexanol H2O ( 1 ) Hg(OAc) 2 / THF HC CH2 OH HgOCOCH3 Oxymercuration CH3 (CH2 ) 2CH=CH2 + CH3 (CH2 ) 2 ( 2 ) NaBH4 / H2 O Demercuration (脱 Hg) CH3 (CH2 ) 2 CHCH2 OH H
A mechanism of addition of Hg(oAc)2 (CH3)3C- CH=CH2 Hg OAc (CH3)3C→c—CH2 δ+8 8+ HoaC HbO (CH33C→C—cH2(2)NaBH4/H2O OH HgoAc (CH3)3C—c—cH2 OH H 3.3-DimethyI-2-butanol (94%)
A mechanism of addition of Hg(OAc)2 ( 2 ) NaBH4 H2 O / H2 O (CH3 ) 3 C H C CH2 OH HgOAc (CH3 ) 3 C CH=CH2 + Hg + OAc + − (CH3 ) 3 C H2 C CH2 HgOAc + (CH3 ) 3C H C CH2 OH H 3,3-Dimethyl-2-butanol (94%)
10.6 Hydroboration(硼氢化反 应): Synthesis of organoboranes (有机硼的合成) Hydroboration H—B c—c THE B Alkene Boron hydride Organoborane
10.6 Hydroboration (硼氢化反 应): Synthesis of organoboranes (有机硼的合成） + H B Hydroboration C C H B Alkene Boron hydride Organoborane THF
B2H6+ O: BH Diborane 乙硼烷 THE THF: BH3 BH3 is a Lewis acid (because the boron has only six electrons in its valence shell). It accepts an electron pair from the oxygen atom of THF
B2 H6 + :O THF O: BH3 + - Diborane 乙 硼 烷 THF:BH3 BH3 is a Lewis acid (because the boron has only six electrons in its valence shell). It accepts an electron pair from the oxygen atom of THF