Question

4. Compound A (C9H17N) is an alkaloid. Two stages of the Hofmann elimination reaction occur to remove the nitrogen and yield a mixture of cyclooctadienes identified by catalytic hydrogenation to

cyclooctane. The ultraviolet spectrum of the mixture shows the absence of the conjugated diene (1,3-cyclooctadiene). Deduce and draw the structure of Compound A.

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