PHIL 2130 Chapter Notes - Chapter 2.8: Steric Effects, Heteroatom, Epoxide
6 May 2020
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Next to heteroatom > benzylic/allylic > -1 carbon. Straight chain alkanes oxidation on -1 carbon. -carbon = end carbon; -1 = next to last carbon. -1 = 2 carbon free radical intermediate. Trans product more likely no steric hindrance. Oxidation on carbon that produces trans product. Involves epoxide intermediate: water oxidizes ketone to carboxylic acid, e- transfer from triple bond to o from heme. Can be reached via epoxide intermediate: fe from heme transfers e- to form c=o double bond. Oxidation at any of five h-atoms on ring to form phen. Nih shift intramolecular shift of h-atom during oxidation. Involves tyrosine synthase convert phenylalanine to tyrosine. Product positioning: epoxide forms from benzene c=c double bond, opening of epoxide, - x-atom attacks +ve carbocation. Fe: proton loss due to double bond formation. Benzene very stable reformation favourable. Oh oxidation loss of two h-atoms (as h+ and h- from alcohol oh)
