Notes0623
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Notes0623

Course: CHEM chem 2364, Spring 2009

School: LSU

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Experiment 6: Synthesis of Benzopinacolone A) Photoreductive Coupling of Benzophenone: O sun light OH + OH 1,1,2,2-tetraphenyl1,2-ethanediol (benzopinacol) reduced product O 2 + OH 2-propanol 1,1-diphenylmethanone (isopropyl alcohol) (benzophenone) reducing agent 2-propanone (acetone) oxidized product Mechanism: Initiation: O UV light S1-diradical O intersystem crossing T1-diradical O Propagation: 31 O +...

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6: Experiment Synthesis of Benzopinacolone A) Photoreductive Coupling of Benzophenone: O sun light OH + OH 1,1,2,2-tetraphenyl1,2-ethanediol (benzopinacol) reduced product O 2 + OH 2-propanol 1,1-diphenylmethanone (isopropyl alcohol) (benzophenone) reducing agent 2-propanone (acetone) oxidized product Mechanism: Initiation: O UV light S1-diradical O intersystem crossing T1-diradical O Propagation: 31 O + H OH OH + OH T1-diradical O + OH O + H O Termination: OH + OH OH OH A couple of drops of acetic acid are added because the glass can make the solution basic and cause a side reaction to occur. HO H O Ph2C OH CPh2 O Ph2C OH CPh2 Ph2C O benzophenone OH H OH + Ph2C OH Ph2CH benzopinacol diphenylmethanol (Isopropyl alcohol is a flammable liquid) (Acetic acid is a corrosive liquid) Question: Can tert-butyl alcohol be used instead of isopropyl alcohol in the synthesis of benzopinacol? Explain! B) Synthesis of Benzopinacolone (Pinacol Rearrangement) 32 Benzopinacol rearranges under acidic conditions to form benzopinacolone. is This an example of a Pinacol Rearrangement. O CH3COH I2 heat Tetraphenylethanone (Benzopinacolona) OH O OH (Benzopinacol) Mechanism: OH OH OH OH H OAc OH2 O H OAc O In unsymmetrical cases, the aromatic ring with the more electrondonating group will migrate faster. 33 X X OH AcOH OH X Y Y Where Y = Group with higher migratory aptitude (more electron-donating) I2 heat X Y Y O Migratory aptitude: p-methoxyphenyl > p-methylphenyl > phenyl > p-chlorophenyl > p-nitrophenyl Iodine is added to the reaction mixture because it promotes the formation of the carbocation. OH OH Ph2C CPh2 + I2 benzopinacol OH OI HI + Ph2C CPh2 an alkyl hypoiodite OH Ph2C CPh2 + OI Iodine will color the product and therefore has to be removed from the product using a minimum amount of cold ethanol. (Iodine is a corrosive poison) (Ethanol is a flammable liquid) Draw the structure of the major organic product for each of the following reactions. 34 CH3 OH OCH3 O CH3COH I2 heat OH CH3 OCH3 CH3 OH NO2 O CH3COH I2 heat NO2 OH CH3 35

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LSU - CHEM - chem 2364
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