Problem

The alkaloid coniine has been isolated from hemlock and purified. Its molecular formula...

The alkaloid coniine has been isolated from hemlock and purified. Its molecular formula is C8H17N.Treatment of coniine with excess methyl iodide, followed by silver oxide and heating, gives the pure (S)-enantiomer of N,N-dimethyloct-7-ene-4-amine. Propose a complete structure for coniine, and show how this reaction gives the observed product.

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