Chapter H, Problem 4PP

Practice Problem H.4

In 1891 G. Merling transformed tropine (see Practice Problem H.3) into 1,3,5-cycloheptatriene (tropylidene) through the following sequence of reactions:

$\begin{array}{l}\text{Tropine}\left({\text{C}}_{\text{8}}{\text{H}}_{\text{15}}\text{NO}\right)\stackrel{-\text{H2O}}{\to }{\text{C}}_{\text{8}}{\text{H}}_{\text{13}}\text{N}\stackrel{{\text{CH}}_{\text{3}}\text{I}}{\to }{\text{C}}_{\text{9}}{\text{H}}_{\text{16}}\text{NI}\underset{\left(2\right)\text{heat}}{\overset{\left(1\right){\text{Ag}}_{\text{2}}{\text{O/H}}_{\text{2}}\text{O}}{\to }}\\ {\text{C}}_{\text{9}}{\text{H}}_{\text{15}}\text{N}\stackrel{{\text{CH}}_{\text{3}}\text{I}}{\to }{\text{C}}_{\text{10}}{\text{H}}_{\text{18}}\text{NI}\underset{\left(2\right)\text{heat}}{\overset{\left(1\right){\text{Ag}}_{\text{2}}{\text{O/H}}_{\text{2}}\text{O}}{\to }}\text{1,3,5-cycloheptatriene}+{\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{N}+{\text{H}}_{\text{2}}\text{O}\end{array}$

Write out all of the reactions that take place.