Question #44920

Consider three isomeric amines $\mathbf{A}$, $\mathbf{D}$, and $\mathbf{F}$ with the molecular formula $\ce{C7H9N}$.

1. $\mathbf{A}$ cannot be prepared by Gabriel phthalimide synthesis. It reacts with Hinsberg's reagent to form a precipitate insoluble in aqueous $\ce{NaOH}$. Treatment of $\mathbf{A}$ with $\ce{NaNO2/HCl}$ at $273\text{ K}$ yields a yellow oil $\mathbf{C}$.
2. $\mathbf{D}$ can be prepared by Gabriel phthalimide synthesis. Treatment of $\mathbf{D}$ with $\ce{NaNO2/HCl}$ at $273\text{ K}$ produces brisk effervescence of a diatomic gas and a major organic product $\mathbf{E}$.
3. $\mathbf{F}$ cannot be prepared by Gabriel phthalimide synthesis, but its Hinsberg product is completely soluble in aqueous $\ce{NaOH}$. Treatment of $\mathbf{F}$ with $\ce{NaNO2/HCl}$ at $273\text{ K}$ yields a water-soluble salt $\mathbf{G}$ which does not evolve gas. Warming the aqueous solution of $\mathbf{G}$ to $298\text{ K}$ yields $\mathbf{H}$.

Identify $\mathbf{C}$, $\mathbf{E}$, and $\mathbf{H}$ (assuming $\mathbf{F}$ is the para-isomer).