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

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Alkenes are Cleaved via OzonolysisozoneO O OR 1 R 3R 2CCR 4synadditionOOOR 1 C C R 3R 2 R 4Alkene Primary (1°)ozonideR 1 O R 3C CR 2 O O• ozone adds across double bonds to give ozonides• ozonides react further with reducing agents to providecarbonyl compounds• we will not discuss mechanism for this reactionR 4Secondary (2°)ozonidereductionOR 1 R 2OR 2 R 3CarbonylcompoundsUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 34Lecture 12: February 1834
Ozonolyis is a Two Step Processreducing agents;reduce ozonide intermediatepattern = alkene is cut in half and replaced by an oxygenatom at each endcarbonyl product depends on substitution of alkeneUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 35Lecture 12: February 1835
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 28 and 29: Halogen Addition Modification:Aqueo
Page 32 and 33: Epoxides are Preparedvia Alkene Epo
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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