Ethylammonium nitrate, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}
\mathrm{NO}_{3}\), was the first ionic liquid to be discovered. Its melting
point of \(12^{\circ} \mathrm{C}\) was reported in 1914 and it has since been
used as a nonpolluting solvent for organic reactions and for facilitating the
folding of protcins.
(a) Draw the Lewis structure of each ion in ethylammonium nitrate and indicate
the formal charge on each atom (in the cation, the carbon atoms are attached
to the \(N\) atom in a chain: \(\mathrm{C}-\mathrm{C}-\mathrm{N})\).
(b) Assign a hybridization scheme to each \(\mathrm{C}\) and \(\mathrm{N}\) atom.
(c) Ethylammonium nitrate cannot be used as a solvent for some reactions
because it can oxidize some compounds. Which ion is more likely to be the
oxidizing agent, the cation or anion? Explain your answer.
(d) Ethylammonium nitrate can be prepared by the reaction of gaseous
ethylamine, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\), and aqueous
nitric acid. Write the chemical equation for the reaction. What type of
reaction is this?
(e) \(2.00 \mathrm{~L}\) of ethylamine at \(0.960\) atm and \(23.2^{\circ}
\mathrm{C}\) was bubbled into \(2.50 .0 \mathrm{~mL}\) of \(0.240 \mathrm{M}
\mathrm{HNO}_{3}(\mathrm{aq})\) and \(4.10 \mathrm{~g}\) of ethylammonium nitrate
was produced. What were the theoretical and percentage yields of the salt?
(f) Suggest ways in which the forces that hold ethylammonium nitrate ions
together in the solid state differ from those that hold together salts such as
sodium chloride or sodium bromide.
(g) Low-melting salts in which the cation is inorganic and the anion organic
have been prepared. Explain the trend in melting point seen in the following
series: sodium acetate \(\left(\mathrm{NaCH}_{3} \mathrm{CO}_{2}\right)\),
\(324^{\circ} \mathrm{C}\); sodium propanoate \(\left(\mathrm{NaCH}_{3}
\mathrm{CH}_{2} \mathrm{CO}_{2}\right), 285^{\circ} \mathrm{C}\); sodium
butanoate \(\left(\mathrm{NaCH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}
\mathrm{CO}_{2}\right), 76^{\circ} \mathrm{C}\); and sodium pentanoate
\(\left(\mathrm{NaCH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}
\mathrm{CO}_{2}\right), 64^{\circ} \mathrm{C}\).