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

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Stoichiometry of Hydroboration6 xB 2 H 6diglyme2 xB1-butenetributylborane• diglyme is a common solvent• hydroborations typically at room temp.• generally very fast reactionsH 3 C OOO CH 3diglyme: diethylene glycol dimethyl etherUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 8Lecture 12: February 188
Lewis Acid-Base ComplexesBorane is a Lewis Acid & Reducing Agent!Other hydroborating reagents with different reactivitiesmay be prepared by adding Lewis bases to diborane (B2H6)B 2 H 6diboraneB 2 H 6diborane++Otetrahydrofuran (THF)H 3 C S CH 3dimethyl sulfide (DMS)H 3 BOH 3 B•THFH 3 BCH 3SCH 3H 3 B•DMS}B 2 H 6diborane+Ntriethylamine (TEA)H 3 BN(CH 2 CH 3 ) 3H 3 B•TEAUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 9Lecture 12: February 189
Page 1 and 2: CHEM 232Organic Chemistry IUniversi
Page 5 and 6: Boranes - Structure & ElectronicsHH
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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