4-AlkenesOzoneRadicalsSynthesisHLSF07

4-AlkenesOzoneRadicalsSynthesisHLSF07 - 5. Ozonolysis:...

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5. Ozonolysis: Oxidative Cleavage C C R R R H O 3 -78 o C O O C O C R R R H Ozonide not isolated explosive CH 3 SCH 3 or Zn, HCl Reductive Work-up Oxidative Work-up NaOH, H 2 O H 2 O 2 C O R R C R H O C O R R C R OH O *You are not responsible for reproducing the mechanism. I have posted the mechanism of the ozonoide formation on Blackboard for those that are interested.
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Examples of Ozonolysis C C H 3 C H CH 2 CH 3 1. O 3 2. CH 3 SCH 3 1. O 3 2. H 2 O 2 , NaOH, H 2 O 1. O 3 2. H 2 O 2 , NaOH, H 2 O
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http://pubs.acs.org/cen/topstory/8145/8145notw1.html Science, 302, 1053 (2003).
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Ozonolysis Useful for Determining Structure of Unknown Alkenes H O O H H O H O work backwards
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6. HBr Addition Re-visited HBr dark HBr ROOR h ! Br Br 90% 95% Some experimental data Introduction to free radical mechanisms and fishhook notation Heterolytic cleavage: Homolytic cleavage:
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1. Initiation - creation of new radicals i. Peroxides R O O R light (h ! ) OR heat ( " ) O O C C k c a l / m o l ~35 ~85 ii. AIBN = azoisobutyronitrile
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4-AlkenesOzoneRadicalsSynthesisHLSF07 - 5. Ozonolysis:...

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