(+)-Coniine is the toxic component of the poison hemlock, the plant believed to have killed Socrates. Coniine has the molecular formula C₈H₁₇N. When coniine is exhaustively methylated, and the resulting product is then heated with Ag₂O, the mixture of compounds A–C is formed. [Compounds A and B are the (E) stereoisomers.]

Propose a structure for coniine. (The absolute configuration of coniine cannot be determined from the data.)

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Me₂NCH₂CH₂CH₂CH₂CH=CHCH₂CH3 Me₂NCH₂CH₂CH₂CH=CHCH₂CH₂CH3 A B H₂C=CHCH₂CH₂CHCH₂CH₂CH3 T NMe₂