Perbenzoic acid in benzene at 0°C epoxidizes the illustrated allylic derivatives. P is obtained for R=COEt and Q for R=H. Which product pair is correct?
With a free allylic OH, hydrogen bonding to the peracid directs oxygen delivery from the OH face, giving the syn epoxide Q. Acyl protection removes that directing OH interaction; approach from the less hindered opposite face gives anti epoxide P for the propionate. The pair with P anti and Q syn is B.
More Oxidation: Oxidation of alcohols involving metal and non-metal-based (chromium, manganese, DMSO, and hypervalent iodine) reagents. Peracid oxidation of alkenes and carbonyls. Alkenes to diols (manganese and osmium-based reagents), alkenes to carbonyls with bond cleavage (ozonolysis), and alkenes to alcohols/carbonyls without bond cleavage (hydroboration-oxidation). Asymmetric epoxidations (Sharpless and Jacobsen) and Sharpless asymmetric hydroxylation. questions
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