PHIL 2130 Chapter Notes - Chapter 2.9: Aldehyde Dehydrogenase, Oxime, Hydroxylamine
6 May 2020
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Involves breaking c-c bond between carb acid and the c it is attached to. Exception = c-c of two adjacent carbonyl groups: Oxidized to carboxylic acid by aldehyde dehydrogenase: thiol lone pair nucleophilic attack on + c=o. Carboxylic acid + ketone oxidized to co2 and carboxylic acid. Similar oxidation mechanism to alcohol to form thioester (carbonyl: thioester readily oxidized to carboxylic acid. Amine oxidation = replacing h-atom on n with oh. Oxidation of nh2 to hydroxylamine (ho-n-r: oxidation of hydroxylamine to nitroso (-c-n=o, if carbon adjacent to nitroso has h-atom, rearrangement into oxime occurs. Oxidation stops here if no h-atom on adjacent carbon: oxime further oxidized similar mechanism to alcohol oxidation, oxidation of amine to hydroxylamine, oxidation of hydroxylamine to nitrone, spontaneous rearrangement to oxime. If h-atoms on both adjacent carbons, more than one product forms. No h-atom no oxidation to oh group. Oxidation of 3 amine involves lone pair on n-atom: lone pairs form bond with o-atom.
