Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...

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Conditions: HydroborationHHBH• boron is exception to octet rule• sp 2 -hybridized (only 3 valence e - s)• contains an empty p-orbital• strong Lewis acid (electron pair acceptor)• forms 3-bonds (neutral) & 4-bonds (-/ve)“Free” borane (BH 3 ) only exists in gas phase, otherwiseundergoes dimerization to diborane (B 2 H 6 )HHBH+HHBHdimerizationHHBHHBHHboranediboraneUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 6Lecture 12: February 186
Page 1 and 2: CHEM 232Organic Chemistry IUniversi
Page 5: Boranes - Structure & ElectronicsHH
Page 9 and 10: Lewis Acid-Base ComplexesBorane is
Page 11 and 12: Hydroboration-Oxidation is Regiosel
Page 13 and 14: Mechanism of HydroborationH 2 BHCH
Page 15 and 16: Regioselectivity - 2nd RationaleEle
Page 19 and 20: Typical Reaction Conditionsfor Halo
Page 21 and 22: Stereospecific Reactions?stereospec
Page 23 and 24: Halogen Addition DoesNot Involve Sy
Page 25 and 26: Halogen Addition DoesInvolve Haloni
Page 27 and 28: Hyperconjugation (σ C-H →π C=C
Page 29 and 30: Ring Opening ofHalonium Ions is Reg
Page 31 and 32: Expoxides (a.k.a Alkene oxides)•
Page 33 and 34: Examples• any peroxyacid will wor
Page 35 and 36: Ozonolyis is a Two Step Processredu
Page 37 and 38: Retrosynthetic AnalysisHow could yo
Page 39 and 40: Self Test QuestionWhich retrosynthe
Page 41 and 42: Self Test QuestionWhat is the produ

Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...

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