Lecture11outline - I Review The oxidation potential of a...

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I. Review • The oxidation potential of a molecule is the electrochemically determied potential at which a molecule releases an electron • Oxidation potentials are lowered (electron loss is easier) when electron donating groups are incorporated into molecules • Electrons can be removed from aromatic compounds, particularly if good electron donors are positioned on the ring • Ceric ammonium nitrate (CAN, Ce(IV)) is a good reagent for converting hydroquinones (1,4- dihydroxybenzenes) to quinones • This process proceeds through removing an electron from the hydroquinone to form a radical cation followed by the loss of a proton to form a radical, followed by the loss of an electron to form a protonated quinone followed by proton loss • Quinones can be converted to hydroquinones by adding electrons and protons • The facile conversion of quinones to hydroquinones is an important part of metabolism • Metabolism is driven by the conversion of NADH to NAD + , which is the key oxidant in
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