Notes0623 - Experiment 6: Synthesis of Benzopinacolone A)...

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Experiment 6: Synthesis of Benzopinacolone A) Photoreductive Coupling of Benzophenone: O OH 2 OH OH O + + sun light 1,1,2,2-tetraphenyl- 1,2-ethanediol 2-propanol (isopropyl alcohol) reducing agent reduced product oxidized product (benzopinacol) 1,1-diphenylmethanone 2-propanone (acetone) (benzophenone) Mechanism: Initiation: O O O S 1 -diradical T 1 -diradical intersystem crossing UV light Propagation: 31
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1 -diradical O OH H OH OH O H O OH 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. Ph 2 C O CPh 2 OH H Ph 2 C O CPh 2 OH HO Ph 2 C O Ph 2 C OH Ph 2 CH OH benzopinacol benzophenone diphenylmethanol + H OH ( 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)
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