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

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Halogen Addition DoesNot Involve Free CarbocationsHHCH 2 Br• carbocation intermediate are planar (flat)• addition of second halide could approach eitherlobe of empty p-orbital on carbocation• therefore this mechanism is not possible becauseit would not be stereoselectiveUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 24Lecture 12: February 1824
Halogen Addition DoesInvolve Halonium IonsH 3 CH 3 CBrHHBrH 3 CH 3 CBrHHBrH 3 CH 3 CBrH 3 CBrH 3 CBrH HHBrH• electron pair in π-bond form new bond to bromine atom asBr-Br bond breaks• lone pair of electrons on bromine form new bond to alkenecarbon losing a bond at the same time (concerted)• halonium ions (three-membered rings with one halogen) areintermediates; no carbocation intermediatesUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 25Lecture 12: February 1825
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 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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