Question

Coniine, C8H17N, is the toxic principle of the poison hemlock drunk by Socrates. It can be synthesized from acrylonitrile (H2C=CHCN) and ethyl 3-oxohexanoate. The synthesis proceeds as follows: Deprotonation of ethyl 3-oxohexanoate to form enolate anion 1; Michael addition to acrylonitrile to form intermediate 2; Protonation to form Michael adduct 3; Ester hydrolysis and decarboxylation to form oxonitrile 4; Reduction to form oxoamine 5; Cyclization to form imine 6; Catalytic hydrogenation to form Coniine. Draw the structures of oxoamine 5 and intermediate 2.

Answer 1

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