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Coniine, a toxic substance isolated from poison hemlock, - McMurry 8th Edition Ch 3 Problem 95
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SOLVED: CH3 HN Coniine Coniine, CgHyzN, is the toxic principle of the poison hemlock drunk by Socrates It can be synthesized from acrylonitrile (HzC-CHCN) and ethyl 3-oxohexanoate. The synthesis proceeds as follows: Deprotonation of ethyl 3-oxohexanoate to form enolate anion Michacl addition to acrylonitrile to form intermediate 2; 3. Protonation t0 form Michacl adduct 3; Ester hydrolysis and decarboxylation t0 form oxonitrile 4; Reduction to form oxoamine 5; Cyclization to form imine 6; Catalyt
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