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

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Addition of B-H Bonds to AlkenesC C + X YadditionXC CYC C + H BH 2hydroborationH C C BH 2alkene borane alkyl boraneoxidationoxidation is a separate step and requiresa separate set of conditions and reagentsHC COHUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010alcoholSlide 4Lecture 12: February 184
Boranes - Structure & ElectronicsHHBH• 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 )2 x BH 3dimerizationB 2 H 65University of IllinoisboraneUICat Chicago CHEM 232, Spring 2010diboraneSlide 5Lecture 12: February 18
Page 1 and 2: CHEM 232Organic Chemistry IUniversi
Page 3: CHEM 232Organic Chemistry IUniversi
Page 8 and 9: Stoichiometry of Hydroboration6 xB
Page 10 and 11: Oxidation StephydroborationB 2 H 6d
Page 12 and 13: Regioselectivity DeterminedDuring H
Page 14 and 15: Regioselectivity - 1st RationaleSte
Page 16 and 17: Self Test QuestionWhat is the produ
Page 18 and 19: Alkene-Halogen AdditionC C + X Yadd
Page 20 and 21: Halogenation is Stereospecific• a
Page 22 and 23: Stereospecific ReactionsStereospeci
Page 24 and 25: Halogen Addition DoesNot Involve Fr
Page 26 and 27: Anti Addition..-: Br:....Br..:..Br.
Page 28 and 29: Halogen Addition Modification:Aqueo
Page 32 and 33: Epoxides are Preparedvia Alkene Epo
Page 34 and 35: Alkenes are Cleaved via Ozonolysiso
Page 38 and 39: Synthetic RouteHow could you prepar
Page 40 and 41: Self Test QuestionDevise a retrosyn
Page 42 and 43: Self Test QuestionWhich starting ma
Page 44: Quiz & Exam AveragesQuiz 1 = 61%Qui

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

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