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10. Propose the shortest synthetic route for the following transformation. OH 1 = HBr 2 = HBr, HOOH 3 = Br 4 = HSO4

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10. Propose the shortest synthetic route for the following transformation. OH 1 = HBr 2 = HBr, HOOH 3 = Br 4 = HSO4 5 = HSO4, HO, HgSO4 6 = OsO4, NMO 7 = 1) RCOH, 2) H3O+ 8 = ethene OH 9 = xs NaNH,/NH3 10 = H/Pt 11 = H/Wilkinson's Catalyst 12 = H/Lindlar's Catalyst 13 = Na/NH3 14 = 1) 03 2) HO 15 = CH3CHCI a. 9, 15, 9, 15, 12, 6 b. 9, 15, 9, 15, 12, 7 c. 9, 15, 9, 15, 13, 6 d. 9, 15, 9, 15, 13, 7 e. b or c

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