PHIL 2130 Chapter Notes - Chapter 2.4: Hydroxylamine, Alcohol Dehydrogenase, Nitrone

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Forms intermediate carbon with free radical, then alcohol. Formation of ketene, then (exception: ethinyl estradiol) carboxylic acid. Transfer of hydride & loss of proton to form aldehyde or ketone (one step) Transfer of hydride & loss of proton to form quinone (=o) Formation of thiohemiacetal, then transfer of hydride & loss of proton to form ketone, then hydrolysis of thioester to form carboxylic acid. Breakage of c-c bond if 2 carbonyl groups are next to each other, to form carboxylic acid (with 1 carbonyl) Formation of hydroxylamine (n-oh), then nitroso (c-n=o), then if proton can be lost on c, then forms oxime (c=n-oh) with 2 r groups. Formation of amine oxide (n(+)-o( )) with 3 r groups. Formation of hydroxylamine (n-oh), then nitrenium ion (r- Hn(+)) if charge can be stabilized, or nitroso. Oxidize 1st h into oh, then dehydrate (h2o) to form diazine (rn=nh), then oxidize 2nd h into oh to form diazonium ion (r-

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