(1)-Coniine is the toxic component of the poison hemlock, the plant believed to have

Chapter 23, Problem 23.25

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(1)-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 AC 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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