Q4 B-Damascenone belongs to a family of fragrant natural products called rose ketones that have been used in the perfume

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Q4 B Damascenone Belongs To A Family Of Fragrant Natural Products Called Rose Ketones That Have Been Used In The Perfume 1 (33.32 KiB) Viewed 47 times

Q4 B-Damascenone belongs to a family of fragrant natural products called rose ketones that have been used in the perfume industry. In one synthesis of B-damascenone, the reaction of compound 1 with one equivalent of MCPBA afforded two constitutionally isomeric epoxides (compounds 2 and 3), which were then converted into diol 4 upon treatment with aqueous acid. Identify the structures of epoxides 2 and 3, and propose a mechanism that converts each of them into compound 4 in the presence of H20. (Note: It is reasonable to presume that a protonated epoxide can open by itself, without the involvement of a nucleophile, if doing so will give a resonance-stabilized allylic carbocation intermediate.)? OH OCH OCH, но MCPBA (one equiv.) 2+3 OH Damascenon