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

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Halogen Addition Modification:Aqueous Solutions Give Halohydrinsbromohydrin• if the solvent for the reaction is changed to water,halohydrins are formed• since water is much more concentrated, it will add tohalonium ion intermediate faster than the halideUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 28Lecture 12: February 1828
Ring Opening ofHalonium Ions is RegioselectiveH 3 CH 3 CBrHHBrH 3 CH 3 CBrHHBrOH 2H 3 CH 3 CHOHBrH HOH 2H 3 CH 3 CHOH 3 CHH 3 CBrH HHBrH• product is most substituted alcohol;least substituted halide• most substituted carbon is mostpartially positively charged intransition state = strongestelectrophile = water most attractedto that carbonUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 29Lecture 12: February 1829
Page 1 and 2: CHEM 232Organic Chemistry IUniversi
Page 5 and 6: Boranes - Structure & ElectronicsHH
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 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

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